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The New York Chemistry Students’ Association
STUDENT AFFILIATE COMMITTEE – NEW YORK SECTION
American Chemical Society
Dr. Raifah M. Kabbani, Co-Chair
Department of Chemistry
Pace University
1 Pace Plaza
New York, NY 10038
rkabbani@pace.edu
tel: 212-346-1621
Dr. Jill Rehmann, Co-Chair
Department of Chemistry
St. Joseph’s College
245 Clinton Avenue
Brooklyn, New York 11205
jrehmann@sjcny.edu
tel: 718-636-7242
May 1st, 2004
Welcome to the 52st Annual Undergraduate Research Symposium of the New York
Chemistry Students' Association. For the past 52 years this meeting has given
undergraduate chemistry students an opportunity to present the results of his or her
research in various fields of chemistry. In addition to affording you the experience of
presenting a scientific paper, the symposium is an oportunity for you to learn about the
research carried out by other students.
The New York Chemistry Students'Association is proud of its 52 year tradition and we
are pleased to offer each of you the opportunity of participating in a marvelous learning
experience. Congratulations on your achievements and we hope that you enjoy sharing
the results of your hard work with your colleagues from other schools.
Dr. Raifah M. Kabbani, Co-Chair
Department of Chemistry
Pace University
Dr. Jill Rehmann, Co-Chair
Department of Chemistry
St. Joseph’s College
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NEW YORK CHEMISTRY STUDENTS'ASSOCIATION
Student Affiliate Committee Members, 2003-2004
Professor Raifah Kabbani, Pace University (New York City), Co-Chair
Professor Jill Rehmann, St. Joseph’s College, Co-Chair
Professor Sasan Karimi, Queensborough Community College, Host
Professor Paris Savronos, Queensborough Community College, Host
Professor Pete Irigoyen, Queensborough Community College, Host
Proffessor William Hersh, Queens College
Professor James A. Ciaccio, Fordham University
Professor Shahrokh Saba, Fordham University
\
Professor Richard D. Cassetta, College of New Rochelle
Professor Neil D. Jespersen, St. John'
s University
Professor Pamela Kerrigan, College of Mount Saint Vincent
Professor Alwell Nwankwoala, Purchase College, SUNY
Professor Nanette Wachter, Hofstra University
Professor Nancy Goroff, Stonybrook University, SUNY
Professor Yorke Rhodes, New York University
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The American Chemical Society Student Affiliate Chapters
of the following Colleges are Members of the
New York Chemistry Students'Association
Adelphi University
L. I. University, C.W. Post College
Barnard College
Manhattan College
College of Mount Saint Vincent
Memorial Sloan-Ketting Cancer Center
College of New Rochelle
Mercy College
Columbia University
Monmouth University
Cooper Union
Mount Sinai School of Medicine
CUNY, Baruch College
New York City Technical College
CUNY, Brooklyn College
New York University
CUNY, City College
New Jersey City University
CUNY, Hunter College
New Jersey Institute of Technology
CUNY, Lehman College
Pace University, New York City
CUNY, Medgar Evers College
Pace University, Pleasantville
CUNY, Queens College
Polytechnic University
CUNY, College of Staten Island
Queensborough Community College
CUNY, York College
Ramapo College of New Jersey
Fairleigh Dickinson University
St. John'
s University
Fordham University
St. Joseph'
s College
Hofstra University
St. Peter'
s College
Hunter College
Southhampton Colleges
Iona College
SUNY, College at Purchase
John Jay College of Criminal Justice
SUNY, Stony Brook University
LaGuardia Community College
SUNY, College at Old Westbury
L. I. University, Brooklyn
Wagner College
Yeshiva University
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SESSION MODERATORS
Moderator
Representing
Room
Dana Canuso
Fordham University
M-140
Anna Radziwon
Fordham University
M-142
Eve Stenson
Fordham University
MC-21
Tanaia Reid
College of New Rochelle
MC-33
Giau Nguyen
College of New Rochelle
MC-32
Lacy-Ann Landell
College of New Rochelle
MC-31
Jasmine Esclara
Pace University
MC-30
Tatiana Hatchett
Pace University
MC-29
Nadia Hussain
Pace University
MC-28
Howard Scneider
Queensborough Community College
MC-41
Erin Robinson
Queensborough Community College
MC-41
Julio Cesar Romero
Queensborough Community College
SS-111
Sherman Belle
Queensborough Community College
SS-112
Octavia Monica
Nicolescu
Queensborough Community College
SS-111
Nia Gibson
Queensborough Community College
SS-112
Kendrick Attidar
Queensborough Community College
M-143
Sang H. Lee
Queensborough Community College
M-143
Alternate Moderator
Mara Mathias
Queensborough Community College
Dory Londorio
Queensborough Community College
Samantha Williams
Queensborough Community College
Ajayee Burgess
Queensborough Community College
Marvin Tobias
Queensborough Community College
Wayne Narain
Queensborough Community College
Imranul Haque
Queensborough Community College
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The New York Chemistry Students’ Association
52nd Annual
Undergraduate Research Symposium
Queensborough Community College
Bayside, NY 11364
Saturday, May 1, 2004
8:00
Registration
Coffee, Tea, Juice, Bagels and Danish
Medical Arts Building M-146
8:30
Welcoming Remarks
Medical Arts Building, M-136
Prof. Jill Rehmann,
Prof. Vijaya Korlipara
Dr. Eduardo Marti
Co-Chair, Student Affiliate Committee
Chair, ACS New York Section
President, Queensborough Community
College
(introducer for Speaker)
9:00
Keynote Address
Medical Arts Building, M-136
Dr. John B. Fenn
Virginia Commonwealth University
"Electrospray Wings for Elephants"
10:15
Group Photo
Stairs between Library and
Administration Building
10:30 Presented Papers - Session I
Analytical & Bioanalytical Chemistry
Biochemistry
Inorganic Chemistry
Nano- & Surface Chemistry
Organic Cemistry
Polymer Chemistry
11:30
Coffee Break
Lobby of the Medical Arts Building
11:45 Presented Papers - Session II
Analytical & Bioanalytical Chemistry
Biochemistry
Inorganic Chemistry
Organic Chemistry
Polymer Chemistry
1:15
Luncheon
Student Union Building
Presentation of Certificates
Prof Raifah Kabbani
Co-Chair, Student Affilates Commitee
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Keynote speaker
Nobel Laureate in Chemistry, 2002
John B. Fenn
The highlight of this year's symposium is the Keynote Address to be delivered by Dr. John B. Fenn,
Nobel Laureate and Professor of Chemistry at Virginia Commonwealth University. Prof. Fenn is the
author of more than 100 papers in scientific journals, a book and has also received 19 patents.
Keynote Address
“Electrospray Wings for Elephants”
John B. Fenn
Electrospray Ionization Mass Spectrometry (ESIMS) has had a long history. Lord Rayleigh developed the
theoretical basis for the method in 1883, and early experiments were carried out by John Zeleny at Yale
during World War I. Otto Stern introduced molecular beam methods in Germany after that war, and this
work was advanced by Isidor Rabi and his disciples at Columbia University after World War II. The
technology evolved with the change from effusive to convective sources for such beams, and some
imaginative but disappointing experiments by Malcolm Dole in the late 1960'
s. Then, in the 1980'
s, Lady
Luck chose our laboratory at Yale for successful achievement of Dole'
s goal; the production and mass
spectrometric analysis of intact ions from very large and fragile molecules such as proteins and
carbohydrates, the molecules that play a vital role in the processes of living systems. ESIMS had since
become a major tool in the discovery and evaluation of new drugs as well as in elucidation of the
biochemical processes on which all living systems depend.
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ANALYTICAL CHEMISTRY
Room: SS-111
Moderator: Julio Cesar Romero, Queensborough Community College
10:30
CALCULATION OF THE IONIZATION CONSTANT OF CARBOXYLIC ACIDS USING
MICROSCALE FREEZING POINT DEPRESSION MEASUREMENTS. Nilda Montes1, Luke
Choi2 , Pedro Irigoyen1, Peter Wong1 and Paris Svoronos1. 1Department of Chemistry, Queensborough
Community College of CUNY, Bayside NY 11364.
2
Benjamin Cardozo High School, Bayside NY 11364.
10:45
IDENTIFICATION OF A SOLUTE’S MOLECULAR WEIGHT USING MICROSCALE
FREEZING POINT DEPRESSION MEASUREMENTS. Luke Choi1, Nilda Montes2, Pedro
Irigoyen2, Peter Wong2 and Paris Svoronos2. 1 Benjamin Cardozo High School, Bayside NY 11364. 2
Department of Chemistry, Queensborough Community College of CUNY, Bayside NY 11364.
11:00
REACTION OF CRYSTAL VIOLET WITH SODIUM HYDROXIDE: A
KINETIC STUDY. Jorge Ubillus, Pedro Irigoyen and Paris Svoronos. Department of
Chemistry, Queensborough Community College, Bayside, NY 11364.
11:15
CALCULATION OF PARTITION COEFFICIENTS OF SUBSTITUTED BENZOIC ACIDS: A
COMPARISON OF SOLVATION MODELS. Junwoong Hwang, Daqing Gao, Department of
Chemistry, Queensborough Community College of CUNY, Bayside, NY 11364
Room: SS-111
Moderator: Octavia Monica Nicolescu, Queensborough Community College
11:45
A CALORIMETRIC DETERMINATION OF THE ENTHALPY OF A DOUBLE
DISPLACEMENT REACTION AND THE APPLICATION OF HESS’S LAW. Tahmeeda
Nazreen, Peter Wong, Pedro Irigoyen and Paris Svoronos. Chemistry Department, Queensborough
Community College, Bayside NY 11364.
12:00
ELECTRONIC ABSORPTION SPECTRA OF UNIVERSAL INDICATORS. Dorra Kridis, Irina
Rutenburg, Pedro Irigoyen, Department of Chemistry, Queensborough Community College of The City
University of New York, Bayside, NY 11364
12:15
DETERMINATION OF THE COMPLEX-FORMATION CONSTANT BETWEEN COPPER
(II) AND GLYCINE BY pH-METRIC MEASUREMENTS. Ishmael Amu, Gerald Ledbetter,
Christina McArthur, Clara Wu, Natural and Applied Sciences Department, LaGuardia Community
College, City University of New York, Long Island City, NY 11101
12:30
pKa OF ACETATE IN AQUEOUS SOLUTION. Hughton Walker, Peter Wong, and Daqing Gao,
Department of Chemistry, Queensborough Community College of CUNY, Bayside, NY 11364
Room: SS-112
Moderator: Sherman Belle, Queensborough Community College
10:30
CHEMISTRY OF BREATHALYZERS, Jude Poku and Pamela Brown,
New York City College of Technology, 300 Jay Street, Brooklyn, N.Y, 11201
10:50
A NOVEL DETERMINATION OF TRANS- FATTY ACIDS USING A NEW COMPUTERAIDED ALGORITHM AND ATR-FTIR. Joyce Fung, John Bove, The Cooper Union for the
Advancement of Science and Art, 51 Astor Place, New York, NY 10003
11:10
DETERMINATION OF ETHANOL CONTENT IN AQUEOUS SOLUTIONS USING ATRFTIR SPECTROSCOPY AND A NEW COMPUTER-AIDED ALGORITHM, Min Hsuan Kuo and
John Bové , The Cooper Union for the Advancement of Science and Art, 51 Astor Place, New York, NY
10003
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Room: SS-112
Moderator: Nia Gibson, Queensborough Community College
11:45
QUANTITATIVE ANALYSIS OF OVER-THE-COUNTER ECHINACEA PREPARATIONS BY
USING HIGH PERFORMANCE LIQUID CHROMATOGRAPHY TO DETERMINE VARIOUS
DETECTION LIMITS OF VARIOUS PHENOLIC ACIDS Taneisha James and Barbara Hillery,
Department of Chemistry, SUNY Old Westbury, Old Westbury, NY 11568
12:05
INVESTIGATING THE ‘CAF’ IN ‘DECAF’ Sanda Stoian and Barbara Hillery
Dept. Of Chemistry, SUNY/Old Westbury, Old Westbury, NY 11568
12:25
CALCIUM ANALYSES IN RACCOON FECES AND TURTLE EGGSHELLS. Diana Froehlich,
Susan Felice, Russell Burke and Sabrina Sobel, Departments of Chemistry and Biology, Hofstra
University, Hempstead, NY 11549
12:45
IDENTIFICATION AND QUANTIFICATION OF AFLATOXINS IN FOOD. Nilda Montes1,
Pedro Irigoyen1, Paris Svoronos1 and Kathryn Emmanuel2. 1Chemistry Department, Queensborough
Community College, Bayside NY 11364 and U.S. 2Food and Drug Administration, Northeast Regional
Laboratory, Jamaica, NY 11433.
Room: M-140
10:30
10:50
11:10
Room: M-140
11:45
12:05
12:25
12:45
Moderator: Dana Canuso, Fordham University
KINETIC STUDY OF AN AMMONIA DETECTION PROCEDURE. Tracey Evans , Judith B.
Weinstein-Lloyd, Chemistry / Physics Department, State University of New York, Old Westbury, NY
11590.
THE SEARCH FOR METHANE ON MARS
Amy Farrell, Br. R. Novak, Yashira Cabral, Timothy Dunne, Boncho Bonev
Department of Physics, Iona College, New Rochelle NY, 10801
MAPPING HDO IN THE MARTIAN ATMOSPHERE Yashira Cabral, Br. R. Novak, Amy Farrell,
Timothy Dunne, Boncho Bonev, Department of Physics, Iona College, New Rochelle NY, 10801
Moderator: Dana Canuso, Fordham University
AN INVESTIGATION OF BROMINATED FLAME RETARDANTS IN PLASTICS. Peter
Anello, Department of Chemistry, SUNY College at Old Westbury, Old Westbury, New York 115680210
SPECTROPHOTOMETRIC ANALYSIS OF ORTHOPHOSPHATE IN THE WATERS OF
NEW YORK CITY. Timothy C. Rodriguez, Fredes B. Dura, Natural and Applied Sciences
Department, LaGuardia Community College, Long Island City, NY 11101
DELIQUESCENCE, EFFLORESCENCE, AND PARTICLE SIZE CHANGE OF SODIUM
CHLORIDE AND MIXED SODIUM CHLORIDE/ DICARBOXYLIC ACIDS. Wes L. Reid, Susan
Oatis, Department of Chemistry, Southampton College, NY 11968
ANALYSIS OF THE CHEMICAL SHIFT CHANGES IN THE 13C NMR OF IODOALKYNES
DUE TO COMPLEXATION WITH LEWIS BASES. Walter N. Moss, Nancy S. Goroff, Department
of Chemistry, State University of New York, Stony Brook, New York 11794
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BIOANALYTICAL CHEMISTRY
Room: M-142
10:30
10:50
11:10
Moderator: Anna Radziwon, Fordham University
X-RAY CRYSTALLOGRAPHY ANALYSIS OF PROTEINS, FOR STRUCTURE AND
FUNCTION DETERMINATION. Mohammad Faisal Halim, Pathways Bioinformatics Center, The
City College of New York, New York, NY 10031.
ANALYSIS OF DNA EXPRESSION DATA FROM OLIGONUCLEOTIDE MICROARRAYS
(PREPARED BY THE AFFYMETRIX GENECHIP SYSTEM) USING THE SOFTWARE
BIOCONDUCTOR. Shams Rashid, Pathways Bioinformatics Center, The City College of New York,
New York, NY 10031
PROBING THE INTERACTION BETWEEN PROTEINS AND SOME SMALL
MOLECULES: FLUORESCENCE STUDY Nkemdirim Emmanuel†, Saida Bibi‡, Raza Alvi‡ and
Ruel Desamero‡ †Queensborough Community College, Bayside, NY 11364 and ‡York College, Jamaica,
New York, NY 11451
BIOCHEMISTRY
Room: M-143
10:30
10:45
Moderator: Kendrick Attidar, Queensborough Community College
PHYTOCHROME A MEDIATED PHOTOMORPHOGENESIS IN ARABIDOPSIS
Lesley-ann Nelson1, Dr. Patricia Schneider1, Dr. Timothy Short2. 1Department of Biology,
Queensborough Community College, Bayside, New York; 2 Dartment of Biology, Queens College,
Flushing, New York.
THE EFFECTS OF TRACE ELEMENTS ON THE INHIBITORY ACTION OF THIOUREA
DURING TYROSINASE MEDIATED CONVERSION OF L- 3, 4
DIHYDROXYPHENYLALANINE TO DOPACHROME. Marcella Powell1, Simran Sehmi1, Paris
Svoronos2 and Patricia Schneider1. 1Department of Biological Sciences and Geology and 2Department of
Chemistry, Queensborough Community College, Bayside NY 11364.
11:00
11:15
Room: M-143
11:45
12:05
12:25
DISTRIBUTION OF PERIODONTAL PATHOGENS IN FAMILIES OF ADULT
PERIODONTAL PATIENTS. Jose Flor, Vanessa Hernandez, Dr. Raji Subramaniam, Dr. Patricia
Schneider, and Dr. Regina Sullivan. Department of Biology, Queensborough Community College,
Bayside, NY 11364.
PREVALENCE OF PERIODONTAL BACTERIA AMONG ASIAN INDIANS WITH
PERIODONTAL DISEASE. Evelyn Teran, Merlyn Brito, Dr. Raji Subramaniam, Dr. Regina Sullivan,
and Dr. Patricia Schneider. Department of Biology, Queensborough Community College, Bayside, NY
11364.
Moderator: Sang H. Lee, Queensborough Community College
OPTICAL PROPERTIES OF YEAST PROTEIN. Harriet Itoka, Jacquelin Rodriguez, Dr. Peter
Wong, Dr. Patricia Schneider, Dr. Tak Cheung, Dr. Alex Flamholz, Dr. David Lieberman. Departments
of Chemistry, Biology and Physics, Queensborough Community College, Bayside, New York 11364.
INVESTIGATION OF YEAST CELL SIZE WITH OPTICAL DIFFUSION. Troy Minott, Janie
Quizhpi, Dr. Tak Cheung, Dr. Alex Flamholz, Dr. David Lieberman, Dr. Peter Wong, and Dr. Patricia
Schneider. Departments of Physics, Chemistry, and Biology, Queensborough Community College,
Bayside, New York 11364.
INTERSTRAND CROSSLINK-INDUCED RECOMBINATION IN DNA REPAIR-DEFICIENT
YEAST CELLS. Yin-Yin Kyi, Shaila Ahmed, Rod Arad, and Wilma Saffran, Department of
Chemistry and Biochemistry, Queens College, New York, NY 11367
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Room: M-142
11:45
12:05
12:25
Room: M-21
10:30
10:50
11:10
Room: M-21
11:45
12:05
12:25
Room: M-31
11:45
12:05
12:25
Moderator: Anna Radziwon, Fordham University
SEQUENCE
REQUIREMENT
FOR
FORMATION
OF
STABLE
G−
−QUADRUPLEX STRUCTURES. Aleena Joseph1,2, Dinshaw J. Patel2, Anh Tuan
Phan2, 1The City College of New York, NY, NY 10031; 2Structural Biology Program,
Memorial Sloan−Kettering Cancer Center, NY,NY 10021
USING AN ADAMANTANE SCAFFOLD TO BUILD THREE-DIMENSIONAL
CHROMOPHORES FOR FRET STUDIES Mariangela Rivera, Zachary E. Katsamanis, Nancy S.
Goroff, Chemistry Dept. at Stony Brook University, Stony Brook, NY 11790
(allow 40 minutes for this presentation)
THE PHOTOTHERAPEUTIC TREATMENT OF C6 CELLS USING WATER SOLUBLE AND
WATER INSOLUBLE PORPHYRINS. Dara Reeves and Tanya Smith Dr. James Haley, Dr. Pamela
Kerrigan, Department of Chemistry and Biochemistry, Manhattan College/College of Mount Saint
Vincent
Moderator: Eve Stenson, Fordham University
CAN SCHIZOPHRENIA BE AN INDICATION FROM A PROTEIN IN SUS SCROFA? STUDY
OF STRUCTURE AND FUNCTIONS IN P00371
Hai Yan Gaw, Bioinformatics Workshop, The City College of New York
INHIBITION OF MATRIX METALLOPROTEINASE 2 EXPRESSION IN EMBRYONIC
CHICK (Gallus, gallus) CULTURES USING A SMALL INHIBITORY RNA (SiRNA)
OLIGONUCLEOTIDE Alex Bertalovitz & Jamie Robbins, Department of Biology, Iona College,
New Rochelle, NY. 10801.
THE EFFECT OF ETHANOL EXPOSED CHICK EMBRYOS ON MMP-2 EXPRESSION. Tyler
G. Merkeley & Jamie Robbins, Iona College, Department Biology, New Rochelle, NY 10801
Moderator: Eve Stenson, Fordham University
EXPLORATION OF STRUCTURAL BASIS OF 5HTIB FUNCTION: A COMPARATIVE
MOLECULAR MODELLING APPROACH. Ashley S Doane, Yuying Gosser, Pathways Science
Center, Department of Chemistry, The City College of New York, New York, NY 10031
HEAVY METAL COMPLEXATION OF PHENYL AND N-METHYL PHENYL
MERCAPTOACETAMIDES: PROBING RELEVANCE OF NON-COVALENT FORCES IN
METALLOCYSTEINATE PROTEINS Patrick Hyypolite, Duncan Quarless, PhD, Robert Hoyte,
PhD. SUNY College of Old Westbury, Old Westbury, NY, USA.
HIGH CALORIC DIET INTAKE DELAYS MOTOR IMPAIRMENT AND MORTALITY IN A
MOUSE MODEL OF AMYOTROPHIC LATERAL SCLEROSIS. Nelson Humala1 J.Suh2, L.Ho2
and G.M.Pasinetti2, Department of Psychiatry, Mount Sinai School of Medicine, New York, NY, USA
Moderator: Lacy-Ann Landell, College of New Rochelle
MUTUAL ENHANCEMENT OF ANTIBACTERIAL ACTIVITY OF LUPULONE AND THE
CYCLIC PEPTIDE POLYMYXIN B. Venkata B.Ambati, Ioana Andrei, Mihaela Leonida, Gerhard J.
Haas, SONS, Fairleigh Dickinson University, Teaneck, NJ.
PEG DERIVATIVE USED FOR BIOCONJUGATION IN ONE- AND TWO-ENZYME
SYSTEMS.Yuegao Huang, Alberto Clavijo, Mihaela D. Leonida, SONS, Fairleigh Dickinson
University, Teaneck, NJ
SYNTHESIS OF PEGYLATED-FMOC-AMINO ACIDS: APPLICATION IN SOLID PHASE
PEPTIDE SYNTHESIS. Jordan Watson and Arthur M Felix, Ramapo College of New Jersey,
Theoretical and Applied Sciences, Mahwah, NJ 07430
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INORGANIC CHEMISTRY
Room: M-33
10:30
10:50
11:10
Room: M-33
11:45
12:05
12:25
Room: M-32
10:30
10:50
11:10
Room: M-32
11:45
12:05
12:25
Moderator: Tanaia Reid, College of New Rochelle
SOLVATION INFLUENCE ON THE ENERGENTICS OF PHOTOINDUCED ELECTRON
TRANSFER REACTIONS IN PORPHYRIN-QUINONE DYADS. Isaac J. Pflaum and Fernando O.
Raineri, Department of Chemistry, SUNY at Stony Brook, Stony Brook, NY 11794
REMOVING THE BARRIER TO FAST OXYGEN REDUCTION BY PHOTO-INDUCED
CHARGE TRANSFER AT ADSORBATE-COVERED SILVER. Michael R. Blair, Anna K.
Radziwon, John J. McMahon, Department of Chemistry Fordham University, Bronx, NY 10458
AN ANALYTICAL STUDY OF THE COMPLEX [Fe(nta)Cl2 ]2- AND ITS PROPERTIES
Jacqueline Chaparro, Marc A. Walters, Department of Chemistry, New York University, NY 10003
Moderator: Tanaia Reid, College of New Rochelle
SYNTHESIS OF PYRIDYLPORPHYRIN OSMIUM(II) DYADS Mahpara Khaliq, Rukya Ali,
Maria Orphanide, Urooj Javed, Xuilan Wang, Virgnia Seng, Farah Charles Pierre, Shemille
Collingswood, Joseph Capritto, Pantea Menhaji, Elise G. Megehee and Alison Hyslop, Department of
Chemistry, St. John'
s University, Jamaica, NY 11439.
ELECTROCHEMICAL STUDY OF RHODIUM(III) POLYPYRIDYL COMPLEXES.
Christopher Emmel and Elise G. Megehee, Department of Chemistry, St. John’s University, Jamaica,
NY 11439.
CHARACTERIZATION OF NEW MIXED LIGAND RHODIUM(III) COMPLEXES. Daniel
Amarante and Elise G. Megehee, Department of Chemistry, St. John'
s University, Jamaica, NY 11439.
Moderator: Giau Nguyen, College of New Rochelle
THE EFFECT OF PARTICLE SIZES AND COMPOSITION VARIATIONS ON RATE OF
APATITE FORM IN SOL-GEL DERIVED BIOGLASS. Olajide Alawode, Safiyyah Hossain, Dr.
Adeniji, Dr. Aderemi Oki. Department of Chemistry & Biochemistry, Long Island University, Brooklyn,
NY 11201
HYDROGEN BONDING COUNTERIONS IN [4Fe-4S] CLUSTERS OF FERRODOXIN
MODEL COMPLEXES Cara Roche, Marc. A. Walters Department of Chemistry, New York
University, New York, NY 10003
TETRACHLOROMETALLATES OF 1,4-DIAZABICYCLO[2.2.2]OCTANE. Ada Gjyrezi and
Raifah Kabbani. Department of Chemistry and Physical Sciences, New York, NY 10038.
Moderator: Giau Nguyen, College of New Rochelle
FINE TUNING LIGANDS FOR USE IN HYDROFORMYLATION REACTIONS WITHIN
IONIC LIQUIDS., Nawras Harsouni, Christi Gandham, Jyothsna Singavarapu, Richard J. Rosso,
Department of Chemistry, St. John’s University, Jamaica, NY 11439
THE SYNTHESIS OF NOVEL COBALT COMPEXES CONTAINING TRIPOD LIGANDS AS
MODELS FOR POTENTIAL HYDROFORMYLATION CATALYSTS. Seda Bilginer and Stephen
Anderson, School of Theoretical and Applied Sciences, Ramapo College of New Jersey, Mahwah, NJ
07430
THE SYNTHESIS OF Di-ACYL COMPLEXES OF IRON AND TUNGSTEN AS
ISOELECTRONIC MODELS OF β-DIKETONATES . Zafar Iqbal and Stephen Anderson, School
of Theoretical and Applied Sciences, Ramapo College of New Jersey, Mahwah, NJ 07430
12
NANO AND SURFACE CHEMISTRY
Room: M-31
10:30
Moderator: Lacy-Ann Landell, College of New Rochelle
NANOWIRES OF TUNGSTEN AND MOLYBDENUM OXIDE PREPARED BY
ELECTROSPINNING Katarzyna M. Sawicka, M. Karadge, A. K. Prasad and P. I. Gouma
Material Science and Engineering Department, St. John'
s University, 8000 Utopia Parkway, Jamaica,
NY 11439
10:50
11:10
SYNTHESIS AND CHARACTERIZATION OF VARIOUS CDA-Cl REVERSE MICELLES.
Pamela Tadross, Marc Walters, Department of Chemistry, New York University, New York, NY, 10003
SELECTIVE MODIFICATION OF β-CYCLODEXTRIN FOR USE AS A
SUPRAMOLECULAR SCAFFOLD. Jason A. Estrada, Zachary E. Katsamanis and Nancy S. Goroff,
Department of Chemistry, SUNY Stony Brook, Stony Brook, NY 11794-3400
ORGANIC CHEMISTRY
Room: MC-41
Moderator: Howard Schneider, Queensborough Community College
10:30
TOTAL SYNTHESIS OF THE SESQUITERPENOID YLANGENE
Julia Christodoulou and Sasan Karimi, Department of Chemistry and Biochemistry, Queens College,
Flushing NY 11367 and Department of Chemistry, Queensborough Community College, Bayside NY
11364
10:45
CONFORMATION OF THE SESQUITERPENOID PRECURSOR OF LONGIFOLENE USING
NMR SPECTROSCOPY. Richard Gastel, Sasan Karimi, and Gopal Subramaniam, Department of
Chemistry, Queensborough Community College, Bayside, NY 11364 & Department of Chemistry &
Biochemistry, Queens College, Flushing, NY 11367
11:00
FREE RADICAL CHLORINATION OF 1o, 2o, AND 3o BENZYLIC HYDROGENS.
Shinsung Lee, Sasan Karimi, David Locke, Gopal Subramaniam, Paris Svoronos,
Department of Chemistry, Queens College and Queensborough Community College of CUNY
11:15
SELECTIVE DEPROTECTION OF D-6,3-GLUCURUNOLACTONE ESTERS Halimatu Sadiya
Mohammed, Therese Soosairaj,, Panayiotis Meleties, Department of Chemistry, Bronx Community
College of the City University of New York, E. 181 St. & University Ave., Bronx, NY 10453
Room: MC-30
Moderator: Jasmine Esclara, Pace University
10:30
THE DIELS-ALDER ADDUCTS OF PERIODOBUTATRIENE AND
PERBROMOBUTATRIENE Obianauju C. Nduka and Nancy S. Goroff,
Department of Chemistry, Stony Brook University, Stony Brook, NY 11794
10:50
11:10
BOROHYDRIDE REDUCTION OF QUINOXALINES
Elena Savrides and Dr. Terrence Gavin, Iona College
EFFICIENT PREPARATION OF ACYCLIC AMIDINIUM SALTS BY ORTHOESTER
EXCHANGE AND AMIDINIUM SALT TRANSAMINATION. Marinda M. Rivera, Shahrokh Saba,
Adeline Kojtari, Peter D’Amico, Dana Canuso, and Moses K. Kaloustian, Department of Chemistry,
Fordham University, Bronx, New York 10458
13
Room: MC-30
Moderator: Jasmine Esclara, Pace University
11:45
SYNTHESIS OF PHOSPHINES FROM PYRILIUM SALTS AND TETRAKIS
(HYDROXYMETHYL) PHOSPHONIUM CHLORIDE, Kelly Daggett, Dr. James McCullagh,
Manhattan College, Riverdale NY, 10471
12:05
ACCIDENTAL SYNTHESIS OF BENZAZEPINES: PREPARATION OF 2,4-DIARYL-3H-1BENZAZEPINES Myra Cheng, Shaan Alli, Richard Leung, Michelle Washington, Keith Ramig,
Department of Natural Sciences, Baruch College, CUNY, 17 Lexington Ave., New York, NY 10010;
Linas V. Kudzma, Baxter Healthcare Corporation, Anesthesia and Critical Care, 95 Spring St., New
Providence, NJ 07974
12:25
NEW STRATEGY FOR THE SYNTHESIS OF ISOFLURANE ENANTIOMERS Shaan Alli,
Myra Cheng, Keith Ramig, Department of Natural Sciences, Baruch College, CUNY, 17 Lexington
Ave., New York, NY 10010
12:45
A GENERAL HIGH YIELDING SYNTHESIS OF ISOCYANIDES, Kathryn Bardsley and Victor
Cesare, Department of Chemistry, St. John'
s University, Jamaica, NY 11439.
Room: MC-41
Moderator: Erin Robinson, Queensborough Community College
11:45
NEW POLYPHOSPHORUS AMIDE ANALOGUES. Zeba Izhar, Chris Massone, Robert Engel,
Department of Chemistry, Queensborough Community College, Bayside, NY 11364, and Department of
Chemistry, Queens College, Flushing, NY 11365.
12:00
NEW HEXACOORDINATED PHOSPHORUS COMPOUNDS. Jennifer West, Chris Massone,
Robert Engel, Department of Chemistry, Queensborough Community College, Bayside, NY 11364, and
Department of Chemistry, Queens College, Flushing, NY 11365.
12:15
PROPOSED SYNTHESIS OF 1-T-BUTYL-3-(4-NITROPHENYL) AZIRIDINONE
12:30
12:45
Nadege Beaulieu1; Ralph Stephani2; Luis A.Vargas1. 1Department of Chemistry, Queensborough
Community College, Bayside, New York. 2 Department of Pharmaceutical Science, St. John’s
University, Jamaica, New York.
SYNTHESIS OF 1, 3-DI-T-TERT-BUTYLAZIRIDINONE (2) AND CLEAVAGE WITH
TRIS(TRIMETHYLSILYL)PHOSPHITE (TMSP) Jiang Yang1; Ralph Stephani2; Luis A. Vargas1.
1
Department of Chemistry, Queensborough Community College, Bayside, New York. 2 Department of
Pharmaceutical Science, St. John’s University, Jamaica, New York.
SYNTHESIS OF 1-(1-ADAMANTYL)-3-T-BUTYLAZIRIDINONE AND CLEAVAGE WITH
TRIS(TRIMETHYLSILYL)PHOSPHITE (TMSP) Shazim Mobin1, Ralph Stephani2, Luis Vargas
A.1. 1Department of Chemistry, Queensborough Community College, Bayside, New York, 2 Department
of Pharmaceutical Science, St. John’s University, Jamaica, New York.
Room: MC-29
Moderator: Tatiana Hatchett, Pace University
10:30
SYNTHESIS OF ARYL-5-(5-PHENYLPENTYL) DERIVATIVES VIA ONE STEP PROCESS.
Daffadil Williams and Kwesi Amoa, Department of Physical, Environmental, and Computer Sciences,
Brooklyn, New York 11225
10:50
SELECTIVE DEPROTECTION OF D-6,3-GLUCURUNOLACTONE ESTERS Therese
Soosairaj, Halimatu Sadiya Mohammed, Panayiotis Meleties, Department of Chemistry, Bronx
Community College of the City University of New York, E. 181 St. & University Ave., Bronx, NY
10453
11:10
SYNTHESIS OF PEGYLATED INSULIN FRAGMENTS: MODEL COMPOUNDS FOR SITESPECIFIC PEGYLATION OF INSULIN. Ashley Carbone and Arthur M. Felix, Ramapo College of
New Jersey, Theoretical and Applied Sciences, Mahwah, NJ 07430
14
Room: MC-29
11:45
12:05
12:25
Moderator: Tatiana Hatchett, Pace University
BIS- AND TRIS-BRANCHED PEGYLATING REAGENTS: CONJUGATION TO COOHTERMINAL AND NH2- TERMINAL PEPTIDES. Rajintha M. Bandaranayake and Arthur M. Felix,
School of Theoretical and Applied Sciences, Ramapo College of New Jersey, Mahwah, NJ 07430
ELECTROCHEMICAL OXIDATIONS OF PROTECTED PYRROLIDINES AND PROLINE
DERIVATIVES Cara Boutte, Dr. S.E. Watson, Dept. of Chemistry, Long Island University.
CHE RESEARCH ABSTRACTS: QUANTIFYING THE CONTRIBUTION OF DIFFERENT
SUBSTITUENTS TO 1, 3-ALLYLIC STRAIN. Nan Wang Department of Chemistry, SUNYStonyBrook, New York, NY 11794-3400
POLYMER CHEMISTRY
Room: MC-28
Moderator: Nadia Hussain, Pace University
10:30
CHARACTERIZATION OF NEW TYPES OF ETHER CONTAINING IONIC LIQUIDS. Annu
Ipe,1Carolyn Spence,1 Delroy Coleman,2 Wadson Miranda,2 Robert Engel2 and Sharon Lall-Ramnarine.1
1
Department of Chemistry, Queensborough Community College, CUNY, Bayside, NY 11364.
2
Department of Chemistry and Biochemistry, Queens College, CUNY, Flushing, NY 11367
10:50
SYNTHESIS OF NEW TYPES OF ETHER CONTAINING IONIC LIQUIDS. Carolyn Spence,1
Annu Ipe,1 Carolyn Spence,1 Delroy Coleman,2 Wadson Miranda,2 Robert Engel2 and Sharon LallRamnarine.1 1Department of Chemistry, Queensborough Community College, CUNY, Bayside, NY
11364. 2Department of Chemistry and Biochemistry, Queens College, CUNY, Flushing, NY 11367
11:10
PREPARATION AND INVESTIGATION OF POLYAMMONIUM HYDROGEL AGAROSE.
Teshell K. Greene, Renee Carrington, Nadia Hussain, JaimeLee I. Cohen, Department of Chemistry and
Physical Sciences, PACE University, New York, NY 10038
Room: MC-28
Moderator: Nadia Hussain, Pace University
11:45
SYNTHESIS AND INVESTIGATION OF ANTIMICROBIAL ALGINATES. Renee Carrington,
Tatiana Hatchett, Teshell Greene, Nadia Hussain, JaimeLee Cohen, Department of Chemistry and
Physical Sciences, PACE University, New York, NY 10038
12:05
IDENTIFYING POLYMERIC BIOMATERIALS: THE ADSORPTION OF LYSOZYME ON
THE POLY (N-ALKYL ACRYLATES) Jennifer Tucci, Robert Mentore, School of Theoretical and
Applied Sciences, Ramapo College of New Jersey, Mahwah, NJ, 07430
12:25
THE INFLUENCE OF MOLECULAR WEIGHT ON MONOLAYER CHARACTERISTICS OF
POLY(METHYL METHACRYLATE).Marylynne Andrews and Robert Mentore, Ramapo College of
New Jersey, School of Theoretical and Applied Sciences, Mahwah, NJ 07430.
15
ANALYTICAL CHEMISTRY
CALCULATION OF THE IONIZATION CONSTANT OF CARBOXYLIC ACIDS
USING MICROSCALE FREEZING POINT DEPRESSION MEASUREMENTS. Nilda
Montes1, Luke Choi2 , Pedro Irigoyen1, Peter Wong1 and Paris Svoronos1. 1Department of
Chemistry, Queensborough Community College of CUNY, Bayside NY 11364.
2
Benjamin Cardozo High School, Bayside NY 11364.
The use of freezing point depression measurements of aqueous solutions using a computer interface leads
to the calculation of the van’t Hoff factor, i, of ionic solutes. Increasing the solute concentration leads to the
formation of ion pairs and subsequent reduction of the i value. Under conditions of dilute solutions, the
calculation of the ionization constant of weak carboxylic acids is feasible. Such solutions involve 5-6g of
water and 0.1-0.3g of the carboxylic acid.
IDENTIFICATION OF A SOLUTE’S MOLECULAR WEIGHT USING
MICROSCALE FREEZING POINT DEPRESSION MEASUREMENTS. Luke Choi1,
Nilda Montes2, Pedro Irigoyen2, Peter Wong2 and Paris Svoronos2. 1 Benjamin Cardozo
High School, Bayside NY 11364. 2 Department of Chemistry, Queensborough Community
College of CUNY, Bayside NY 11364.
Freezing point depression measurements of solutions have been extensively used to identify the nature of
the solute. Traditional experiments involve large quantities of both the solute and solvent and subsequent
accumulation of large quantities of waste material. The use of a computer interface allows the identification
of the solute’s molecular weight with quantities as low as 4g of the solvent and 0.1g of the solute. Typical
molecular weight accuracy is within + 1 amu. The results of various solvent/solute mixtures that involve
solid/solid, solid/liquid and liquid/liquid combinations are presented
REACTION OF CRYSTAL VIOLET WITH SODIUM HYDROXIDE: A
KINETIC STUDY. Jorge Ubillus, Pedro Irigoyen and Paris Svoronos.
Department of Chemistry, Queensborough Community College, Bayside, NY
11364.
The kinetics of the reaction of crystal violet with sodium hydroxide at different concentrations has been
studied via a computer interface program using green LED light source at 590nm. The order of reaction
with respect to each of the reactants as well as the rate constant, were determined. Kinetic measurements at
different temperatures were also obtained enabling the calculation of the energy of activation for the
reaction.
R1
R
H2/Cat. H+
R2
R3
R1
O
R2
R3
R4
R
R4
CALCULATION OF PARTITION COEFFICIENTS OF SUBSTITUTED BENZOIC
ACIDS: A COMPARISON OF SOLVATION MODELS. Junwoong Hwang, Daqing Gao,
Department of Chemistry, Queensborough Community College of CUNY, Bayside, NY
11364
Free energy of solvation is important in controlling the activities of organic molecules in solution. Thus
much effort has been made to develop models that can accurately calculate solvation free energies of both
neutral molecules and charged ions. In this study, we used different methods that are available in Gaussian
03 and Cramer and Truhlar’s solvation models to calculate the free energies of solvation of several parasubstituted benzoic acids in chloroform, toluene and water. These implicit solvation models generated
results that are used to calculate the free energy of transfer of these molecules from water to chloroform
and to toluene, which can give the partition coefficients.
16
A CALORIMETRIC DETERMINATION OF THE ENTHALPY OF A DOUBLE
DISPLACEMENT REACTION AND THE APPLICATION OF HESS’S LAW. Tahmeeda
Nazreen, Peter Wong, Pedro Irigoyen and Paris Svoronos. Chemistry Department,
Queensborough Community College, Bayside NY 11364.
The reaction between crystalline barium hydroxide octahydrate and solid ammonium thiocyanate in a
calorimeter resulted in a slurry of solid barium thiocyanate and gaseous ammonia, accompanied by a large
drop in temperature of the reaction mixture, indicating high endothermicity of the reaction. A parallel
reaction between potassium thiocyanate and barium hydroxide only engendered a modest temperature drop,
suggesting low endothermicity. The discrepancy in the very different values of ∆Hrxn for the two
apparently similar reactions is accounted for by the secondary reaction:
NH4++OH-→ NH3 + H2O,
the equilibrium being shifted to the far right because of the strong base from the hydroxide. Quantitative
measurements are in progress to evaluate the magnitude of ∆H for the reaction:
NH4+ + OH- → NH3(g) + H2O(l) by applying Hess’s Law.
ELECTRONIC ABSORPTION SPECTRA OF UNIVERSAL INDICATORS. Dorra
Kridis, Irina Rutenburg, Pedro Irigoyen, Department of Chemistry, Queensborough
Community College of The City University of New York, Bayside, NY 11364
We have created a data base in terms of electronic absorption spectra (as fingerprints) corresponding to
integer values of pH for Yamada'
s mixture of indicators (universal indicator), extract of red cabbage, and
extract of beets. The project takes advantage of the property of indicators to change color at a certain pH
and the property of a mixture of indicators to undergo multiple color change with a change in pH.
Yamada'
s universal indicator is a mixture of various indicators carefully designed to manifest the whole
rainbow of colors as a function of pH; red cabbage and beets are naturally occurring mixtures with the
same properties. Solutions of pH were made and adjusted to integer, from 0 to 14, using nitric or
hydrochloric acids and sodium hydroxide. The spectra of each solution with Yamada'
s universal indicator,
red cabbage, and beets were taken, using Ocean Graphics 2000 PC UV/visible spectrophotometer. Spectral
changes and their correspondence to various colors as function of pH were studied, analyzed, and tabulated.
The spectral fingerprints we have created can be used to teach beginning chemistry students about
electronic absorption by compounds and interpretation of molecular absorption spectra, since in the first
year of chemistry only atomic absorption and spectra are discussed. Experiments or theoretical studies can
be designed for students of different levels, both one year and one semester courses of general chemistry as
well as chemistry for nonscience majors.
DETERMINATION OF THE COMPLEX-FORMATION CONSTANT BETWEEN
COPPER (II) AND GLYCINE BY pH-METRIC MEASUREMENTS. Ishmael Amu,
Gerald Ledbetter, Christina McArthur, Clara Wu, Natural and Applied Sciences Department,
LaGuardia Community College, City University of New York, Long Island City, NY 11101
Copper(II) sulfate is a blue-colored solution. When it reacts with glycine, the blue color becomes more
intense. We hypothesize that the following complex-formation reaction is taking place:
Cu2+ + nNH2CH2COO- = [Cu-(NH2CH2COO)n](2-n), where n is the coefficient for NH2CH2COO- in the
chemical equation.
By gradually adding incrementally a weighed amount of glycine to a prepared copper(II) sulfate solution of
known concentration, the pH changes were followed. The data were collected using a pH probe and
LabWork (II) interfaced with a computer.
Our results indicate that n = 2 for the complex-formation reaction. The Kf value is determined to be
+ 0.1) x 1015.
17
pKa OF ACETATE IN AQUEOUS SOLUTION. Hughton Walker, Peter Wong, and
Daqing Gao, Department of Chemistry, Queensborough Community College of CUNY,
Bayside, NY 11364
High-level ab initio molecular orbital calculations and combined quantum mechanical and molecular
mechanical Monte Carlo simulations were performed to calculate the absolute value of pKa for the acetate
anion (CH3CO2-) as a carbon acid in aqueous solution. The computed pKa of 32.4 is in good agreement with
the experimentally determined value of 33.5. Both the computational details and biological implications of
this research will be addressed. D.G. acknowledges the support of the Chemistry Department of QCC for
this research program.
CHEMISTRY OF BREATHALYZERS, Jude Poku and Pamela Brown,
New York City College of Technology, 300 Jay Street, Brooklyn, N.Y, 11201
Half the automobile fatalities in this country are alcohol related. The breathalyzer is one tool to determine
blood alcohol. The objective of this research is to develop a general chemistry laboratory to demonstrate
the principles behind the breathalyzer, which utilizes the color change associated with the reaction between
ethanol and acidic potassium dichromate solution:
8H+ + Cr2O7-2 + 3C2H5OH → 2Cr +3 + 3C2H4O + 7H2O
The equipment employed is the Vernier visible spectrometer. To simulate breath alcohol,
the air above five different concentrations of ethanol was collected separately and
bubbled through equal amounts of yellow acidic potassium dichromate solution. As the
ethanol concentration increased the solution gradually changed from yellow to blue. The
absorption of the samples was then measured using the visible spectrometer and values of
absorbance versus concentration were obtained. To correlate the link between the blood
alcohol and the measured breath alcohol, we employed Henry’s law:
Pbreath = k[Ethanol]blood
Hence with a known Henry’s law constant and the breath alcohol content, the blood alcohol content can be
determined.
A NOVEL DETERMINATION OF TRANS- FATTY ACIDS USING A NEW
COMPUTER-AIDED ALGORITHM AND ATR-FTIR. Joyce Fung, John Bove, The
Cooper Union for the Advancement of Science and Art, 51 Astor Place, New York, NY
10003
FDA has regulated that by 2006 all food products sold must be labeled with the amount of trans fatty acid
content. This means that all manufacturers of food must measure and label the amount of trans fat using an
FDA accepted technique.
Mixtures of various oils with differing percentages of elaidic acid are made and spectra are obtained using
Attenuated Total Reflectance Fourier Transform Infrared Spectroscopy (ATR-FTIR). Elaidic acid is the
most common trans fatty acid in most foods. To find the amount of trans fat, a program is then used,
IRA2003. One of us has developed a computer aided pattern recognition of infrared spectra. This
technique has now been advanced to perform quantitative analysis. A rho value is found and this rho value
is the difference between integration values. The generated rho values are then plotted versus percent trans
in the oil. A calibration curve is produced using these rho values. Calibration curves can then be used to
measure the amount of trans fat in foods. Sesame oil, which has 0% trans fat, has been used with elaidic
acid to generate these calibration curves. Rho values have been compared to 100% elaidic acid and also to
100% sesame oil, with R2 values of 0.9771 and 0.9619 respectively. Any calibration curve may be crossreferenced with another to check the precision of the analysis.
18
DETERMINATION OF ETHANOL CONTENT IN AQUEOUS SOLUTIONS USING
ATR-FTIR SPECTROSCOPY AND A NEW COMPUTER-AIDED ALGORITHM, Min
Hsuan Kuo and John Bové , The Cooper Union for the Advancement of Science and Art, 51
Astor Place, New York, NY 10003
A new analytical method using attenuated total reflectance Fourier transform infrared(ATR-FTIR)
spectroscopy has been developed to determine the concentration of ethanol in aqueous solutions. This
computer-aided technique is based on an algorithm developed at the Cooper Union.1 The algorithm
involves the comparison of two infrared spectra by taking the difference of their normalized integration
values. This difference is called a rho value. Using this technique, calibration curves of rho versus ethanol
concentration are generated. It is found that integration in the wavenumber interval of 3000 cm-1 to 1000
cm-1 yields the best results. Standard mixtures having ethanol concentrations of 0-100% (both by volume
and by weight) were prepared in a glove box. One percent increments were used for the concentration
ranges of 10 to 20% ethanol, and 5% increments were used for other concentrations. Using the spectrum of
pure 200 proof ethanol as the reference, and choosing the integration range of 3000 cm-1 to 1000 cm-1, the
calibration curve of rho v.s ethanol concentration yielded a straight line with a correlation coefficient of
0.9972. This efficient and sensitive technique can be applied in the analysis of alcoholic beverages for their
ethanol contents.
--------------------------------------------
1 "Computer-aided pattern recognition of organic infrared spectra". Shabsi Walfish, Timothy Sosnowski, Sara Shraibman, Lok Yung and
John Bové. Internet Journal of Vibrational Spectroscopy 5, 2nd. ed. (2001).
QUANTITATIVE ANALYSIS OF OVER-THE-COUNTER ECHINACEA
PREPARATIONS BY USING HIGH PERFORMANCE LIQUID
CHROMATOGRAPHY TO DETERMINE VARIOUS DETECTION LIMITS OF
VARIOUS PHENOLIC ACIDS Taneisha James and Barbara Hillery,
Department of Chemistry, SUNY Old Westbury, Old Westbury, NY 11568
Echinacea, or purple coneflower, is best known for its immune enhancing ability. It is used for a variety of
medicinal purposes. Of the several varieties of Echinacea, the three species most commonly used
medicinally are purpurea, angustifolia, and pallida. Many chemical components have been identified in
Echinacea extracts. While no federal standard exists for these nutraceuticals, it has been suggested that
standardization be based on phenolic acid content. Phenolics present in Echinacea include caffeic acid and
derivatives such as chlorogenic acid, chicoric acid, and caftaric acid.
In this work, we compared several brands of over-the-counter Echinacea preparations. These nutraceuticals
varied greatly in price and label ingredients. There were also variations in phenolic acid composition.
Analyses were performed using High Performance Liquid Chromatography with a 250 x 4.6 mm C-18
column and UV detection at 330 nm. Detection limits were determined for caffeic acid and chlorogenic
acid standards. The linear dynamic range for these compounds was over 5 orders of magnitude with a
coefficient of determination of 0.9992 to 0.9990, respectively.
INVESTIGATING THE ‘CAF’ IN ‘DECAF’ Sanda Stoian and Barbara Hillery
Dept. Of Chemistry, SUNY/Old Westbury, Old Westbury, NY 11568
While coffee and tea contain a host of chemicals, the one that concerns people most is the caffeine. In an
attempt to avoid caffeine, many people turn to decaffeinated beverages, though this may not always be
sufficient. A product may contain anywhere between 2 and 13 mg of caffeine and still be labeled
“decaffeinated”. Additionally, human errors exist; anecdotes abound of caffeinated coffee being substituted
for “decaf” ordered at your local restaurant. This work investigates this anecdotal evidence. Samples of
decaffeinated coffee and tea were obtained locally and analyzed for caffeine. Samples were extracted using
solid phase extraction (SPE) and analyzed by reverse phase high performance liquid chromatography (HPLC)
with uv detection.
19
CALCIUM ANALYSES IN RACCOON FECES AND TURTLE EGGSHELLS. Diana
Froehlich, Susan Felice, Russell Burke and Sabrina Sobel, Departments of Chemistry and
Biology, Hofstra University, Hempstead, NY 11549
Raccoons predate ca. 92% of about 2050 terrapin (turtle) nests laid each year on the island of Ruler’s Bar
Hassock in Jamaica Bay, NY. Presumptive nest holes are counted annually to monitor terrapin
reproductive effort, and holes remaining after nests are predated are distinguished from other holes by the
presence of eggshells left behind after predation. We found evidence that raccoons dramatically change
their predation behavior during the 2 month terrapin nesting season; in the second month they often eat
eggs entirely and leave no eggshell remains. To determine the relative amount of terrapin eggs eaten by
raccoons, we have turned to analyzing calcium in raccoon feces. Standard EDTA titration of digested feces
was used, after adapting the ashing process for the samples. In addition, we have started to analyze intact
terrapin eggshells to determine calcium content. Terrapin eggshells are rubbery in texture and consist of a
mixture of aragonite and protein matrix, therefore one cannot assume that they are pure CaCO3. We plan to
correlate the two sets of results to quantify eaten eggs per feces sample.
IDENTIFICATION AND QUANTIFICATION OF AFLATOXINS IN FOOD. Nilda
Montes1, Pedro Irigoyen1, Paris Svoronos1 and Kathryn Emmanuel2. 1Chemistry Department,
Queensborough Community College, Bayside NY 11364 and U.S. 2Food and Drug
Administration, Northeast Regional Laboratory, Jamaica, NY 11433.
Mycotoxins are toxic metabolites produced by certain fungi that can infect and proliferate on various
agricultural commodities in the field and/or during storage. Aflatoxins, Patulin, Deoxynivalenol(DON),
Fumonisins and Ochratoxin A are specific mycotoxins that may be teratogenic, mutagenic, and/or
carcinogenic in animal species. Aflatoxins are metabolic products of the molds Aspergillus flavus and
Apergillus parasiticus and usually occur in food as a result of mold growth in substances including peanuts,
corn, Brazil nuts, pistachio nuts, pumpkin seeds and watermelon seeds. Because of their toxicity
Aflatoxins are restricted to the minimum practical levels using modern processing techniques, the current
level being 20 micrograms per kilogram(20 ppb) for human food. To ensure that the level of aflatoxins in a
sample is restricted to the minimum level, several methods can be used, one in particular being liquid
chromatography. Using this method the aflatoxin is identified and quantified.
KINETIC STUDY OF AN AMMONIA DETECTION PROCEDURE. Tracey Evans ,
Judith B. Weinstein-Lloyd, Chemistry / Physics Department, State University of New York,
Old Westbury, NY 11590.
Aerosol particles in the atmosphere have in recent years been linked to health problems in animals
including humans, to climate change, and to poor visibility. One of aerosol’s contributors is ammonia in the
environment, which reacts with nitric acid or sulfuric acid vapor, forming ammonium nitrate or ammonium
sulfate, and transfers gaseous material into the particulate phase in the air. In light of this the United States
Environmental Protection Agency in collaboration with scientists around the country are working on
creating detectors which can sense the presence of ammonia in the air. We are developing an instrument to
detect ammonia through the formation of a fluorescent isoindole by reacting NH4+ and SO3-2 with ophthalaldehyde. We are studying the kinetics of this reaction using a stopped flow injector which allows
real time observation of the increase in fluorescence. The third order rate constant was found to be 1.7 x 102
M-2s-1 at room temperature. The reaction exhibited an Arrhenius dependence on temperature, with an
activation energy of approximately 30 kJ.
20
THE SEARCH FOR METHANE ON MARS
Amy Farrell, Br. R. Novak, Yashira Cabral, Timothy Dunne, Boncho Bonev
Department of Physics, Iona College, New Rochelle NY, 10801
To collect data on Mars’ atmosphere we used NASA’s infrared telescope. It is a 3.0-meter diameter
telescope atop Mauna Kea, 13,796 feet above sea level, on the Big Island of Hawaii. The instrument we
used was C-Shell, an infrared spectrometer that covers the 1.0-5.5 micron spectral range, with a resolution
of 40,000 (λ/∆λ), to collect our data. We tuned the telescope to the Methane absorption bands in the 3.3micron region or the wave number of 3,000 1/cm. At these settings we were able to detect both CH4 and
H2O. We took data at four different CH4 absorption settings, R0 (3028 cm-1), and R1 (3039 cm-1), in
January and March of 2003, and P2 (2999 cm-1), and P4 (2079 cm-1), in January of 2004. I will present
spectra taken at these settings and give an estimate of the amount of Methane in Mars’ atmosphere. I will
also discuss the spectrometer uses and the optics of the telescope. This project was partially funded
through a grant from the NSF-RUI program (AST-0205397).
MAPPING HDO IN THE MARTIAN ATMOSPHERE Yashira Cabral, Br. R. Novak,
Amy Farrell, Timothy Dunne, Boncho Bonev, Department of Physics, Iona College, New
Rochelle NY, 10801
Our goal was to collect spectroscopic HDO data from Mars’ atmosphere and make a global map of the
results. For our data collection we used NASA’s Infrared Telescope Facility (IRTF), a 3.0-meter telescope
located on Mauna Kea, in Hawaii. The instrument we used was CSHELL, which is a high-resolution
spectrograph that covers the 1.0 -5.5 micron spectral range and has a maximum resolution of 40,000. It has
a 30” long slit and uses a 256 x 256 array to capture data; spatial resolution is 0.2”/pixel. The HDO data
was captured using a 3.67-micron setting. The date which we collected the data was March 21, 2003 in
which Mars was in its northern summer and there was a Doppler shift of -15 km/s. The slit was positioned
North/South on Mars and stepped at 1.0” intervals to obtain data across the entire disk of Mars. Reduction
of the data was done using Interactive Data Language (IDL). A 2D map of HDO column density for this
date was produced.
AN INVESTIGATION OF BROMINATED FLAME RETARDANTS IN PLASTICS.
Peter Anello, Department of Chemistry, SUNY College at Old Westbury, Old Westbury, New
York 11568-0210
Polybrominated diphenyl ethers (PBDEs) are used as flame retardants in many commercial products such
as televisions, personal computers, Christmas lights, and cushions of furniture to name a few. PBDEs are
known to cause immunosuppression, to have adverse effects on the reproductive system, to disrupt the
endocrine system, and to induce carcinogenicity in rodents. Sources of PBDEs in the environment come
from the incineration of municipal waste and leaching in landfills which may be ingested by insects and
become part of the food chain. PBDEs are being outlawed in Europe and should require closer scrutiny
here. By using FTIR to determine which plastics have these flame retardants in them we can get a better
idea on the amount of use and their effect on the environment.
SPECTROPHOTOMETRIC ANALYSIS OF ORTHOPHOSPHATE IN THE
WATERS OF NEW YORK CITY. Timothy C. Rodriguez, Fredes B. Dura, Natural and
Applied Sciences Department, LaGuardia Community College, Long Island City, NY 11101
Orthophosphates are a known quantity in the New York City water system, used to protect pipes from
corrosion. According to our research, the phosphate content of the water at the watersheds is kept close to
NYC-DEP targets of 15µg/l to 20µg/l. Analysis of the phosphates was performed with an ammonium
vanadomolybdate solution which bonds with phosphate ions to create a yellow solution containing
heteropoly acids which was then measurable with our Spectronic21 spectrophotometer. Water from tap
sources in all five boroughs ranged from 57mg/l up to as much as 86 mg/l; significantly higher than waters
sampled from the East and Hudson rivers, which contained 56-57mg/l.
21
DELIQUESCENCE, EFFLORESCENCE, AND PARTICLE SIZE CHANGE OF
SODIUM CHLORIDE AND MIXED SODIUM CHLORIDE/ DICARBOXYLIC
ACIDS. Wes L. Reid, Susan Oatis, Department of Chemistry, Southampton College, NY
11968
Atmospheric aerosols play a major role in global climate. By scattering solar radiation, aerosols can cool
the earth’s surface directly and compensate for some of the global warning due to greenhouse gases.
Aerosols can also act as cloud condensation nuclei, and therefore affect the cloud albedo. Most of the
literature studies have focused on measuring the physio-chemical properties of aerosols with diameters
larger than 100nm. Below 30-50 nm, the increased curvature of the particle has the effect of increasing the
vapor pressure above the particle. Phase transitions, such as deliquescence where the solid particle absorbs
water and becomes a saturated droplet, are expected to be affected by the Kelvin effect. Field studies have
determined that the composition of aerosols is often a complex mixture of an inorganic salt and an organic
component. While the organic component can often constitute 10-70% by mass of the fine particle mode,
all of the compounds making up the organic portion of the particle have not been identified. Most
laboratory studies have focused on the water-soluble secondary organics, such as dicarboxylic acids. In
order to provide better data for global modeling, we have studied the water uptake of pure NaCl and
internally mixed NaCl/succinic acid particles. Previous studies have reported a change in the growth factor
due to the presence of the organic component, but no change in the deliquescence relative humidity (DRH).
We report the water uptake curves for pure NaCl and internally mixed NaCl/succinic acid particles for
diameters less than 20 nm.
ANALYSIS OF THE CHEMICAL SHIFT CHANGES IN THE 13C NMR OF
IODOALKYNES DUE TO COMPLEXATION WITH LEWIS BASES. Walter N. Moss,
Nancy S. Goroff, Department of Chemistry, State University of New York, Stony Brook,
New York 11794
Iodoalkynes are good Lewis acids and are able to form charge transfer complexes with bases by accepting
electrons into an unfilled σ* orbital. Formation of these complexes leads to deshielding at the alkynyl
carbon directly attached to iodine. The source of this interesting NMR effect has been investigated using
various ab initio computational methods. The 13C NMR shieldings for several iodoalkyne systems have
been calculated at the B3LYP level using a mixed all electron basis set (Sadlej pVTZ for iodine and 6-31G*
for all other nuclei) in the GIAO procedure. The calculations reproduced the observed deshielding effect of
complex formation. The source of this NMR effect has been interpreted within the framework of the
Ramsey Formalism. In this theory, paramagnetic contributions to the chemical shielding arise from
magnetically induced couplings
between filled and virtual MOs. Orbitals have been identified that can interact, leading to the observed
chemical shift changes.
BIOANALYTICAL CHEMISTRY
X-RAY CRYSTALLOGRAPHY ANALYSIS OF PROTEINS, FOR STRUCTURE AND
FUNCTION DETERMINATION. Mohammad Faisal Halim, Pathways Bioinformatics
Center, The City College of New York, New York, NY 10031.
X-ray crystallography has long been used to study the structure of crystalline materials, and with the use of
0.5 Angstrom-2 Angstrom x-rays crystalline materials have been probed into their depths allowing for
diffraction patterns that contain information on entire molecules of crystallized protein. With the vast
amounts of information yielded by x-ray diffraction from large molecules, however, a non-trivial amount of
computational work is required to model the structure of the molecule under analysis. This project models
the structure of protein molecules, using x-ray crystallography methods, for subsequent use in protein
function prediction. This project uses a software called Xplor, developed at and distributed by the Center
for Structural Biology at Yale, run over a network of computers that functions as a cluster, using another
software called Green Tea, from Green Tea Tech. This work presents the methods of crystallography data
analysis, and how those can be applied towards modeling protein crystallography data, and the challenges
and accomplishments of undertaking this task.
22
ANALYSIS OF DNA EXPRESSION DATA FROM OLIGONUCLEOTIDE
MICROARRAYS (PREPARED BY THE AFFYMETRIX GENECHIP SYSTEM)
USING THE SOFTWARE BIOCONDUCTOR. Shams Rashid, Pathways Bioinformatics
Center, The City College of New York, New York, NY 10031
In recent years, use of cDNA microarrays has become increasingly more important in the analysis of DNA
expression data from various genomic experiments. In particular, the Affymetrix GeneChip system has
produced very useful results. The vast quantities of data yielded by each of these experiments require the
use of sophisticated computational software to utilize information obtained. This project investigates the
use of the software Bioconductor and demonstrates how data from oligonucleotide microarrays may be
analyzed. Bioconductor is a fairly novel program that provides functions for efficient analysis of gene
expression data. It was developed primarily by the Biostatistics Unit of the Dana Farber Cancer Institute at
the Harvard Medical School/Harvard School of Public Health and uses the R package system, a program
for statistical computing and graphics. Both Bioconductor and R are open source projects. Apart from the
analysis of gene expression data, Bioconductor provides tools for numerous other bioinformatic functions.
PROBING THE INTERACTION BETWEEN PROTEINS AND SOME SMALL
MOLECULES: FLUORESCENCE STUDY Nkemdirim Emmanuel†, Saida Bibi‡, Raza
Alvi‡ and Ruel Desamero‡ †Queensborough Community College, Bayside, NY 11364 and
‡
York College, Jamaica, New York, NY 11451
This study was done to investigate the spectroscopic characteristics of some biologically important
molecules, like quinine, amino acids, cofactors, L-dopa and tetrahydropteridine, using fluorescence
spectroscopy. For quinine, the effects of concentration, temperature and fluorescence quencher were
studied. The fluorescence measurements revealed that there is a direct linear relationship between
fluorescence intensity and concentration, fluorescence intensity increased proportionately with increased
concentration. Temperature had an inverse effect on the fluorescence intensity of quinine, as the
temperature was increased the intensity of quinine fluorescence decreased. This quenching of quinine
fluorescence was also observed when NaCl, a fluorescence quencher, was added to the solution. It was
evident that as the concentration of NaCl was increased the fluorescence intensity of quinine decreased.
Another aspect of the study was to determine the fluorescence signature of tyrosine, tryptophan, NADH,
NAD+, L-dopa, and tetrahydropteridine. These spectroscopic characterizations were done in preparation for
the third stage of the project which is to investigate interactions between proteins and some of the small
molecules studied here.
23
BIOCHEMISTRY
PHYTOCHROME A MEDIATED PHOTOMORPHOGENESIS IN ARABIDOPSIS
Lesley-ann Nelson1, Dr. Patricia Schneider1, Dr. Timothy Short2. 1Department of Biology,
Queensborough Community College, Bayside, New York; 2
artment of Biology, Queens College, Flushing, New York.
Many of the biochemical reactions responsible for plant growth and differentiation are light-induced. In
higher terrestrial plants, these photomorphisms are usually dependent on long light (red) wavelengths.
Phytochrome A is produced in darkness as PR (P660) which is biologically inactive. Exposure to light of
660nm wavelength transforms this allosteric protein into PFR (FR=far-red) which is biologically active. PFR
is converted back to PR when exposed to light of a wavelength of 730nm. P FR has been shown to be
responsible for many physiological responses in Arabidopsis. This study investigated the role of
phytochrome A in the synthesis of the Arabidopsis pigments, chlorophyll and anthocyanin. Wild type (ws)
Arabidopsis and a mutant deficient in phytochrome A (PhyA) were exposed to different wavelengths of
light. At the end of the 3 to 5 day incubation period, high levels of anthocyanin and low levels of
chlorophyll were detected in the wild type. In contrast, the phytochrome A deficient mutant lacked
anthocyanin but contained high levels of chlorophyll. These results indicate that phytochrome A plays a
role in stimulating anthocyanin production and inhibiting chlorophyll production. Lesley-ann Nelson is a
participant in the QCC-NIH Bridges to the Baccalaureate Program (grant 1 R25 GM65096-01).
THE EFFECTS OF TRACE ELEMENTS ON THE INHIBITORY ACTION OF
THIOUREA DURING TYROSINASE MEDIATED CONVERSION OF L- 3, 4
DIHYDROXYPHENYLALANINE TO DOPACHROME. Marcella Powell1, Simran
Sehmi1, Paris Svoronos2 and Patricia Schneider1. 1Department of Biological Sciences and
Geology and 2Department of Chemistry, Queensborough Community College, Bayside NY
11364.
Tyrosinase, a copper containing oxidoreductase essential for melanin production, is involved in the
oxidation of 3, 4 L- dihydroxyphenylalanine to dopaquinone and subsequent spontaneous conversion to
dopachrome. Thiourea was introduced to the biochemical reaction as a non-competitive inhibitor known to
be responsible for chelating the copper cofactor of tyrosinase, which is necessary for product formation,
consequently decreasing the rate of the reaction. Various trace elements were utilized to investigate their
potential interference with thiourea, therefore possibly restoring the enzymatic activity observed without
inhibition.
DISTRIBUTION OF PERIODONTAL PATHOGENS IN FAMILIES OF ADULT
PERIODONTAL PATIENTS. Jose¢ Flor, Vanessa Hernandez, Dr. Raji Subramaniam,
Dr. Patricia Schneider, and Dr. Regina Sullivan. Department of Biology, Queensborough
Community College, Bayside, NY 11364.
Severe forms of adult periodontal disease are associated with anaerobic gram-negative bacteria, in
particular Prophyromonas gingivalis, Treponema denticola, and Bacteroides forsythus. While there is
evidence that these bacteria can be spread from person to person through saliva, the impact of demographic
variables and household pets on familial infection is largely unknown. This study examined the distribution
and routes of transmission of periodontal bacteria among family members. Two patients, an Asian Indian
male and a Caucasian female, with severe periodontitis were recruited from a private dental practice.
Subgingival plaque samples from these patients, their spouses, children and household dogs were tested for
pathogens by enzyme assay and DNA analysis. The BANA (N-benzoyl-DL-arginine-2napthyamide) test
detected arginine hydrolase, an enzyme produced by all three periodontal pathogens. The polymerase chain
reaction (PCR) detected specific pathogens based on the amplification of signature sequences of the small
subunit16S rRNA genes. We examined the relationship between bacterial distribution, BANA score,
clinical parameters (pocket depth, dental history and bleeding on probing) and demographic variables
(ethnicity, gender and age). Jose¢ Flor and Vanessa Hernandez are participants in the NIH Bridges to the
Baccalaureate Program at Queensborough Community College (grant 1 R25 GM65096-01).
24
PREVALENCE OF PERIODONTAL BACTERIA AMONG ASIAN INDIANS WITH
PERIODONTAL DISEASE. Evelyn Teran, Merlyn Brito, Dr. Raji Subramaniam, Dr.
Regina Sullivan, and Dr. Patricia Schneider. Department of Biology, Queensborough
Community College, Bayside, NY 11364.
Anaerobic gram-negative bacteria, in particular Prophyromonas gingivalis, Treponema denticola, and
Bacteroides forsythus, are associated with severe forms of adult periodontal disease. Demographic
characteristics, such as age, gender and race, have been shown to influence both the incidence of
periodontal disease and the bacterial composition of subgingival plaque. However, the impact of these
factors on Asian populations is largely unknown. This study investigated the prevalence of the three
pathogens in Asian Indian periodontal patients at a private dental clinic. The BANA (N-benzoyl-DLarginine-2-napthyamide) enzyme assay was performed on subgingival plaque samples taken during routine
scaling. DNA was extracted from paper points used by the dentist to collect samples of subgingival fluid.
The polymerase chain reaction (PCR) detected specific pathogens based on the amplification of signature
sequences of the small subunit16S rRNA genes. We examined the relationship between bacterial
distribution, BANA score, demographic factors (age and gender) and clinical parameters (pocket depth,
dental history and bleeding on probing). Evelyn Teran and Merlyn Brito are participants in the NIH Bridges
to the Baccalaureate Program at Queensborough Community College (grant 1 R25 GM65096-01).
OPTICAL PROPERTIES OF YEAST PROTEIN. Harriet Itoka, Jacquelin Rodriguez, Dr.
Peter Wong, Dr. Patricia Schneider, Dr. Tak Cheung, Dr. Alex Flamholz, Dr. David
Lieberman. Departments of Chemistry, Biology and Physics, Queensborough Community
College, Bayside, New York 11364.
Yeast cells were inoculated in Sabouraud Dextrose Broth and incubated in a 300C shaker water bath for 48
hr. The cells were washed and separated into density fractions by centrifuging. The top and bottom layers
of the packed cell volume (PCV) showed density variation of about 15%. Cells from each fraction were
treated with Zymolase to digest the chitin cell wall and then lysed to extract protein. Biuret reagent was
added to the protein extracts and the absorbance of the violet Cu++- protein complex was measured at 540
nm and compared to a BSA standard curve. Preliminary results suggest that high PCV density correlated
with high protein content. When suspensions of cells from each fraction were analyzed with the
spectrophotometer, the resulting absorption spectra suggested higher absorption for cells in the bottom
layer. Optical diffusion profiles for the top and bottom layers are consistent with the protein analysis and
the absorption spectra obtained with cell suspensions. The optical diffusion may prove to be a viable
technique for tissue diagnosis. Harriet Itoka and Jacqueline Rodriguez are participants in the QCC-NIH
Bridges to the Baccalaureate Program (grant 1 R25 GM65096-01).
INVESTIGATION OF YEAST CELL SIZE WITH OPTICAL DIFFUSION. Troy
Minott, Janie Quizhpi, Dr. Tak Cheung, Dr. Alex Flamholz, Dr. David Lieberman, Dr. Peter
Wong, and Dr. Patricia Schneider. Departments of Physics, Chemistry, and Biology,
Queensborough Community College, Bayside, New York 11364.
Yeast cells were inoculated in Sabouraud Dextrose Broth and incubated in a 300C shaker water bath for 48
hr. The cells were washed and separated into density fractions by centrifuging. The top and bottom layers
of the packed cell volume (PCV) showed a density variation of about 15%. Yeast cells were digitally
photographed under 100X oil immersion lens and measured using Mitotic Images Plus 2.0 software. The
bottom layer shows a Gaussian-like distribution with mean at 20 microns. The top layer showed a longer
tail distribution with the mean at 25 microns. Preliminary results suggest that the higher density of the PCV
bottom layer correlated with smaller cell size. The distribution of cell size in the top layer top is consistent
with the distribution reported by John Val and John Tyson in 1996. The optical diffusion profiles for the
top and bottom layers could be modeled with density differences. These results suggest that density is a
viable parameter to characterize yeast. Troy Minott and Janie Quizhpi are participants in the QCC-NIH
Bridges to the Baccalaureate Program (grant 1 R25 GM65096-01).
25
INTERSTRAND CROSSLINK-INDUCED RECOMBINATION IN DNA REPAIRDEFICIENT YEAST CELLS. Yin-Yin Kyi, Shaila Ahmed, Rod Arad, and Wilma Saffran,
Department of Chemistry and Biochemistry, Queens College, New York, NY 11367
Interstrand DNA crosslinks inhibit DNA replication and transcription, and are cytotoxic and mutagenic. In
baker’s yeast the major pathway for crosslink repair involves both nucleotide excision repair (NER) and
homologous recombination (HR). Crosslinks are initially processed to double strand breaks, in a step that
depends on NER and DNA replication. Rejoining of the double strand breaks depends on HR. We have
measured crosslink-dependent repair and recombination in repair-proficient, NER-deficient, and HR-deficient
yeast strains, using a his3 duplication to assay recombination by gene conversion or single-strand annealing.
In repair proficient cells psoralen crosslinking induced recombination, primarily by gene conversion. NERdeficient strains were more sensitive to psoralen damage and had lower levels of crosslink-induced
recombination; the majority of His+ recombination occurred by single-strand annealing rather than gene
conversion. HR-deficient strains were also sensitive to psoralen damage and showed little induced
recombination.
SEQUENCE REQUIREMENT FOR FORMATION OF STABLE
G−
−QUADRUPLEX STRUCTURES. Aleena Joseph1,2, Dinshaw J. Patel2,
Anh Tuan Phan2, 1The City College of New York, NY, NY 10031; 2Structural
Biology Program, Memorial Sloan−Kettering Cancer Center, NY,NY 10021
Guanine−rich DNA sequences are found in a multitude of biologically significant sites such as telomeres,
recombination spots, and gene promoters. They can form four−stranded structures known as
G−quadruplexes, which are built from the stacking of G−tetrads (1). We have explored sequence
requirements for different elements of G−quadruplex topologies. Using Nuclear Magnetic Resonance
(NMR), we demonstrate that the d(GGTTTTGG) sequence forms a dimeric G−quadruplex involving a core
of two G−tetrads and two diagonal loops (2). Examination of a number of other DNA sequences suggests
that (i) T4 is the shortest diagonal loop (ii) two is the minimum number of G−tetrads required for formation
of a stable G−quadruplex in solution.
anti
syn
1
2
USING AN ADAMANTANE SCAFFOLD TO BUILD THREE-DIMENSIONAL
CHROMOPHORES FOR FRET STUDIES Mariangela Rivera, Zachary E. Katsamanis,
Nancy S. Goroff, Chemistry Dept. at Stony Brook University, Stony Brook, NY 11790
Forster Resonance Energy Transfer (FRET) has become a useful tool for molecular biologists in the study
of macromolecules. The transfer of energy between two chromophores is a through-space interaction that
depends on the distance between them. A noted drawback of FRET is that the energy transfer is dependent
not only on the distance between molecules but also on the angular orientation of molecules with respect to
each other. One solution to this limitation is to make isotropic chromophores such that the angular
dependence of FRET is relieved and FRET accuracy is preserved in experiment where chromophore
movement is impaired. Adamantane can serve as a suitable scaffold upon which such an isotropic array
can be made. We are exploring two synthetic routes to attach 3 or 4 chromophores to the bridgehead
positions of adamantane. The first route functionalizes the adamantane bridgeheads with carboxylic acids
and the second route attaches four phenyl groups. These chromophores would provide a new tool for
future FRET studies. This work was supported with funding from the Undergraduate Research & Creative
Activities (URECA) office.
26
THE PHOTOTHERAPEUTIC TREATMENT OF C6 CELLS USING WATER
SOLUBLE AND WATER INSOLUBLE PORPHYRINS. Dara Reeves and Tanya Smith
Dr. James Haley, Dr. Pamela Kerrigan, Department of Chemistry and Biochemistry,
Manhattan College/College of Mount Saint Vincent
Photodynamic therapy is the use of light coupled with the administration of light sensitive porphyrins to
treat malignant cells. Porphyrins are tetrapyrrolic molecules that play an important role in various
biological processes. The response of C6 glial cells to a variety of porphyrins was investigated. The cells
incorporated the porphyrins in vitro. The cells were incubated for a period of 20-24 hours after treatment
with the porphyrins. They were irradiated for an hour and incubated for another 20-24 hours. The controls
lacked porphyrins or were not irradiated. The effect of the porphyrin was determined by cell viability.
Initial results revealed that of the tri-anisyl porphyrin showed the best results. The metallated porphyrins
and the unmetallated porphyrins gave fairly similar results. The water-soluble porphyrin, H2TPPEA, gave
results similar to the tri-anisyl porphyrins. Still, other variables are yet to be tested before more conclusive
results are obtained.
CAN SCHIZOPHRENIA BE AN INDICATION FROM A PROTEIN IN SUS
SCROFA? STUDY OF STRUCTURE AND FUNCTIONS IN P00371
Hai Yan Gaw, Bioinformatics Workshop, The City College of New York
Genomic imprinting in pigs currently searches for the genes involved in obesity, diabetes and
schizophrenia. This study attempted to determine the structure of one of the defected proteins in
schizophrenia based on the genes, which have been found to be responsible in diabetes. We focused on one
type of protein, called D-amino acid oxidase from Sus Scrofa. The D-amino acid oxidase, P 00371, is
classified as alpha-beta protein with antiparallel beta sheet. Using homology modeling, we determined the
structure of a protein, which showed the closest resemblance to the original target protein. Finally, a
similarity between the length of two sequences and high percentage of the residue identity would provide a
strong proof for the final structure.
INHIBITION OF MATRIX METALLOPROTEINASE 2 EXPRESSION IN
EMBRYONIC CHICK (Gallus, gallus) CULTURES USING A SMALL INHIBITORY
RNA (SiRNA) OLIGONUCLEOTIDE Alex Bertalovitz & Jamie Robbins, Department of
Biology, Iona College, New Rochelle, NY. 10801.
Studies show that matrix metalloproteinases (MMPs), a group of enzymes possessing an endopeptidase
activity operating outside the cell in the extracellular matrix, play important roles during embryonic
development by influencing the rates of cellular migration, controlling enzyme activities and activating
growth factors necessary for proper development. The protease under investigation in this laboratory,
MMP-2, is expressed early during vertebrate development and may play an important role in regulating
growth factor signal intensity in the extracellular matrix. To address this question we are trying to inhibit
the expression, and therefore synthesis of MMP-2, using a sequence-specific short inhibitory RNA
(SiRNA) oligonucleotide. MMP-2 expression will be measured in control cultures of embryonic chick
cells and in comparable cultures transfected with the SiRNA. The level of MMP-2 expression will be
measured by the reverse transcriptase polymerase chain reaction (RT-PCR).
27
THE EFFECT OF ETHANOL EXPOSED CHICK EMBRYOS ON MMP-2
EXPRESSION. Tyler G. Merkeley & Jamie Robbins, Iona College, Department Biology,
New Rochelle, NY 10801
Fetal Alcohol Syndrome (FAS) results in birth defects in developing vertebrate embryos when an extreme
level of maternal alcohol digestion occurs. Symptoms of FAS include hypoplasia of the first Branchial
Arch (cleft palate) and cardiac abnormalities. Both types of developmental defects are associated with
defects in neural crest cells (NCC) migration and differentiation. Treating chick embryos with ethanol
inhibits normal migration of neural crest cells. Neural crest cells migration is likely mediated by a family of
extra cellular matrix proteases referred to as matrix metalloproteinases (MMP). The question addressed in
this study is whether ethanol treatment alters levels of activity of a key protease MMP-2. We compared
levels of MMP-2 mRNA expression in control embryos and in embryos treated with ethanol. Twenty Four
hour embryos were injected with 100µL of PBS (control) or a 25% (v/v) solution of Ethanol in PBS
(experimental). Injected embryos were cultured for an additional 24 hours and anterior portions of the
embryos were dissected for further analysis. Analysis of mRNA was measured by the reverse transcriptase
polymerase chain reaction (RT-PCR). Initial results of ethanol treated embryos showed softer tissue and
abnormalities in the neural fold.
EXPLORATION OF STRUCTURAL BASIS OF 5HTIB FUNCTION: A
COMPARATIVE MOLECULAR MODELLING APPROACH. Ashley S Doane, Yuying
Gosser, Pathways Science Center, Department of Chemistry, The City College of New York,
New York, NY 10031.
Abnormalities in 5-HT neurotransmission have been correlated with many neurological and psychiatric
disorders. Further, 5-HT receptors represent important targets for pharmacotherapy. 5HT1B, one of
twelve known 5-HT receptor subtypes, is a 7 transmembrane G protein coupled receptor. There is no
experimentally determined structure of 5HT1B, therefore the exact location of the serotonin binding site on
the three dimensional structure of 5HT1B is unknown. We implemented homology modeling techniques
and used the three dimensional structure of bovine rhodopsin as primary template. The three-dimensional
structure models of 5HT1B generated by homology modeling were further examined by current
biochemical experimental data and the serotonin binding site of 5HT1B was predicted. The binding of
serotonin to 5HTB1 was simulated using a docking simulation program in the MOE software. This
complex structural model remains to be improved and further experimental study is needed for evaluation
of this model.
28
HEAVY METAL COMPLEXATION OF PHENYL AND N-METHYL PHENYL
MERCAPTOACETAMIDES: PROBING RELEVANCE OF NON-COVALENT
FORCES IN METALLOCYSTEINATE PROTEINS Patrick Hyypolite, Duncan Quarless,
PhD, Robert Hoyte, PhD. SUNY College of Old Westbury, Old Westbury, NY, USA.
A series of phenyl meracptoacetamides were synthesized to explore there mimetic relevance for modeling
the structure and reactivity of metallocysteinate proteins that are involved in heavy metal transport. Two
particular ligands were used in this preliminary study, phenyl meracptoacetamide and N-menthyl phenyl
mercaptoacetide. These two ligands were used to probe the significance of structural modifications that
affect non-covalent forces (dipole-dipole interactions) within the ligand. A colorimetric technique with a
complexing indicating, Xylenol Orange, in a non-aqueous protic methanolic solvent is described. The
technique was employed to determine the sensitivity (metal concentration dependence) of the colorimetric
method for a series of divalent heavy metal cations (Zn2+, Cd2 +, Hg2, Cu2+, Pb2+) and one univalent
heavy metal cation (Cu1+). Although mercury was the least sensitive, the method typically was sensitive to
metal chloride concentrations ~ 10-5 M. The visible spectryoscopy of the various solutions was examined
to determine the relative concentrations of complexed and free indicator. Solutions of both single
(homonuclear) and mixed metals [bimetallic (heteronuclear)] were examined in the presence of the
meracaptoacetamide ligands to evaluate in a quantitative manner the general availability of the metals for
complexation with the indicator in the various systems. All of the solutions contained concentration ratios
of 4:1 ligand to metal. By spectroscopic analysis the zinc solutions appeared to be the least discriminate of
the metal citations with respect to the two ligands. The other cations varied in their affinities for the
indicator relative for the indicator relative to the two ligands. The mixed metal solutions typically showed
lower extinctions as contrasted with individual metal solution. These preliminary results suggest a
structural consequence for the presence of non-covalent interactions within these ligand-metal solutions.
These interactions may have importance in producing compounds that model the structure and reactivity of
metalloproteins such as metallothionein.
HIGH CALORIC DIET INTAKE DELAYS MOTOR IMPAIRMENT AND
MORTALITY IN A MOUSE MODEL OF AMYOTROPHIC LATERAL SCLEROSIS.
Nelson Humala1 J.Suh2, L.Ho2 and G.M.Pasinetti2, Department of Psychiatry, Mount Sinai
School of Medicine, New York, NY, USA
Amyotrophic lateral sclerosis (ALS) is a fatal neurodegenerative disease characterized by progressive
muscle weakness and atrophy. Although dysphagia is a common feature of ALS, the nutritional and
metabolic status of ALS patients has received little attention. For example there is evidence that ALS
patients have a chronically deficient intake of energy, thus augmentation of energy intake, rather than the
consumption of high-protein nutritional supplements, may be beneficial to the ALS patient. Based on this
evidence we explored the role of high caloric intake in the G93A human superoxide dismutase-1 (SOD-1)
mouse (referred to as SOD-1G93A) model of ALS. This SOD-1G93A ALS mouse model was generated by
genetic-engineered expression of the G93A mutant form of human SOD-1, which was found in some cases
of familial ALS. Similar to ALS, SOD-1G93A ALS mice present age-dependent motor neuron degeneration
leading to progressive muscle weakness and atrophy. The macronutrient caloric composition of the high
caloric diet was 60% fat (from lard), 20% carbohydrate (refined sucrose) and 20% protein. In parallel
control experiment, a second SOD-1G93A ALS mouse group was fed a normal rodent diet, which is low in
saturated fat (10%) and contained complex carbohydrates (60% starch) and 20% protein. Diet treatments
were initiated at 50 days of age, prior to onset of ALS-type muscle weakness and atrophy. We found that
SOD-1G93A ALS mice fed the high caloric diet showed a trend of slower decline in ALS type motor
impairment compared to SOD-1G93A ALS mice fed normal diet, as assessed by a Rotarod assay.
Interestingly, SOD-1G93A ALS mice fed high caloric diet also showed a trend for increased survival rate.
However, the observed differences in motor impairment and survival rate between SOD-1G93A ALS mice
exposed to the high caloric diet compared to the normal diet did not reach statistical significance, possibly
due to the small number of animals used in this study. Our findings support a potential role for caloric
intake in the pathophysiology of ALS, and suggest that prophylactic augmentation of energy intake might
delay motor dysfunction in the SOD-1G93A transgenic mouse model of ALS. Support Contributed By: ALSA
to GMP.
29
MUTUAL ENHANCEMENT OF ANTIBACTERIAL ACTIVITY OF LUPULONE
AND THE CYCLIC PEPTIDE POLYMYXIN B. Venkata B.Ambati, Ioana Andrei,
Mihaela Leonida, Gerhard J. Haas, SONS, Fairleigh Dickinson University, Teaneck, NJ.
The well publicized problems with resistance of pathogens to antibiotics make it desirable to seek new
entities which have previously not been used for medical treatment. There are many antimicrobial
substances produced by plants; one of them is the hop derived compound lupulone as well as other
antimicrobially active hop constituents. We tested these compounds alone as well as together with other
antimicrobials to find any mutual reinforcement or positive coaction. Such a positive coaction forms the
basis of our research:
the coaction of hop compounds with the peptide antibiotic polymxin B. We established this activity
enhancement with gram positive bacteria using a disc diffusion assay and MIC (Minimum Inhibitory
Concentration) determination.
PEG DERIVATIVE USED FOR BIOCONJUGATION IN ONE- AND TWO-ENZYME
SYSTEMS.Yuegao Huang, Alberto Clavijo, Mihaela D. Leonida, SONS, Fairleigh Dickinson
University, Teaneck, NJ
Polyethylene glycol-succinimidyl succinate (PEG) was used in bioconjugation procedures targeting the low
stability of enzymes. Glutamate dehydrogenase (GDH) and glutaminase (Gase) were covalently linked to
PEG in one-enzyme and two-enzyme settings, respectively. The activities of the pegylated systems were
assessed by spectrophotometric assays and in biosensors for glutamate and glutamine detection. Following
the decrease in activity due to the conjugation, the modified enzymes maintained almost constant activity
for an extended time. The influence of the ratio enzyme(s):PEG on the activity of the bioconjugated
systems was investigated too. The pegylated enzymes were immobilized on carbon paste electrodes
together with a mediator. Different mediators and different immobilization methods were studied. The
nicotinamide cofactor required for GDH was added either to the paste or in solution and the results are
discussed comparatively in the paper. All biosensors studied showed pronounced catalytic effect and
linearity which recommends them for use in the analysis of glutamate and glutamine in biotechnology
applications and clinical lab.
SYNTHESIS OF PEGYLATED-FMOC-AMINO ACIDS: APPLICATION IN SOLID
PHASE PEPTIDE . Jordan Watson and Arthur M Felix, Ramapo College of New Jersey,
Theoretical and Applied Sciences, Mahwah, NJ 07430
Solid phase peptide synthesis is widely used for drug discovery in the pharmaceutical and biotechnology
industries. A major constraint in the solid phase procedure results from incomplete couplings during
assemblage of the peptide on the resin resulting in deletion and/or truncated sequences. These incomplete
sequences are usually acetylated during the solid phase procedure but are often difficult to separate by high
performance liquid chromatography since their hydrophilicity is similar to that of the target peptide.
Pegylation of substrates such as peptides and proteins is known to increase their amphiphilic properties
resulting in improved solubility of the substrate in both organic and aqueous solvents. We are developing a
novel reagent in which poly(ethylene glycol) [PEG-2000] is linked to 9-fluorenylmethoxycarbonyl-amino
acids. These PEG-Fmoc-amino acids can be used for the final coupling reaction in a solid phase synthesis
resulting in PEG-Fmoc-peptide-resin while all deletion peptides are acetylated. Following TFA cleavage
from the resin, the resultant PEG-Fmoc-peptide are fully soluble in water and can be readily separated from
the acetylated deletion peptides by dialysis. In the final stage, the target peptide may be obtained in pure
form by deprotection with piperidine. Preliminary progress on the synthesis of PEG-Fmoc-amino acids and
a system designed to evaluate the dialysis purification of a model tetrapeptide will be discussed.
30
INORGANIC CHEMISTRY
SOLVATION INFLUENCE ON THE ENERGENTICS OF PHOTOINDUCED
ELECTRON TRANSFER REACTIONS IN PORPHYRIN-QUINONE DYADS. Isaac J.
Pflaum and Fernando O. Raineri, Department of Chemistry, SUNY at Stony Brook, Stony
Brook, NY 11794
There is considerable interest in understanding the influence of the environment on the rates of
photoinduced intramolecular electron transfer reactions in solution. Of particular interest are molecular
systems comprising electron-donor and electron-acceptor moieties that are covalently linked by a bridge
group. These molecular dyads are comparatively large and are designed to mimic some aspects of the
natural photosynthetic systems.
In this study we examine the solvation structure (solvent arrangement around the solute) and the electron
transfer solvation energetics (solvation free energy change, solvent reorganization energy, activation free
energy) that determine the rate constants for photoinduced charge separation in selected porphyrin-quinone
dyads in a series of solvents. The solvation structures are calculated with liquid-state integral equation
methodologies and the electron transfer energetics is examined under a renormalized linear response
approximation. The systems considered have either linear (donor-bridge-acceptor) or cyclophane-like
(bridge-supported face-to-face donor and acceptor groups) architectures.
REMOVING THE BARRIER TO FAST OXYGEN REDUCTION BY PHOTOINDUCED CHARGE TRANSFER AT ADSORBATE-COVERED SILVER. Michael R.
Blair, Anna K. Radziwon, John J. McMahon, Department of Chemistry Fordham University,
Bronx, NY 10458
The slow kinetics of the oxygen reduction reaction (ORR) presents a challenge to improving the efficiency
of energy production from fuel cells. Here, we present evidence of photocatalysis of the ORR at adsorbatecovered silver electrodes. The adsorbates used in the experiment were bis-pyridyl acetylene (BPA) and bispyridyl ethylene, unsaturated ligands which bind to the electrode surface through the terminal nitrogens.
We measure increases in the reduction current associated with irradiation of the silver electrode surface in
an electrochemical cell that is saturated with oxygen. Fig. 1 reports the current increase at –150 mV (vs.
Ag/AgCl) upon irradiation. In the absence of light, oxygen does not reduce at this voltage. While the light
is on, the current drops with concentration polarization of dissolved oxygen. At –250 mV (Fig. 2), where
oxygen reduces without light, we observe thermal increases in the current during irradiation. Since
warming by the light must occur at both applied voltages, the warming has no effect on the rate of
photocatalyzed oxygen reduction at –150 mV. These results suggest that no activation energy barrier
hinders the transfer of electrons from the irradiated surface to oxygen, thus perfectly photocatalyzing
oxygen reduction.
Fig. 1.
Irradiation of BPA-covered
silver at –150 mV at 4 sec,
50mW, 5145 Å (Ar+ laser)
31
Fig. 2. Irradiation of BPA-covered
silver at –250 mV at 4 sec,
50mW, 5145 Å (Ar+ laser)
AN ANALYTICAL STUDY OF THE COMPLEX [Fe(nta)Cl2 ]2- AND ITS
PROPERTIES Jacqueline Chaparro, Marc A. Walters, Department of Chemistry, New York
University, NY 10003
The complex (Et4N)2[Fe(nta)Cl2] (Et4N= tetraethyl ammonium, nta= nitrolotriacetate) has been synthesized
and isolated from dimethylformamide (DMF) solution. The Et4N+ and pyH+ (py = pyridine) salt of the
complex are compared by means of X-ray crystallography and UV-vis spectroscopy water and acetonitrile.
Both the pyridinium and tetraethyl ammonium chloride salts of the Fe-nta complex are readily used in the
catalysis of the oxidation of dithiols to disulfides in the presence of oxygen. These synthetic reactions have
been studied using dithiols of 3, 4, and 5 carbons; the products were characterized by mass spectroscopy
and chromatography. The tetraethyl ammonium Fe-nta complex produces better yields in these oxidations.
When comparing the crystal structures of Et4N+ with that of the pyH+ it is evident that the two crystal
structures are isometric except for the the Fe-N bond length, which is 2.208Å in the Et4N+ salt and 2.2355Å
in the pyH+ salt.
SYNTHESIS OF PYRIDYLPORPHYRIN OSMIUM(II) DYADS Mahpara Khaliq, Rukya
Ali, Maria Orphanide, Urooj Javed, Xuilan Wang, Virgnia Seng, Farah Charles Pierre,
Shemille Collingswood, Joseph Capritto, Pantea Menhaji, Elise G. Megehee and Alison
Hyslop, Department of Chemistry, St. John'
s University, Jamaica, NY 11439.
Porphyrin compounds are ubiquitous in nature and play key roles in light harvesting processes in
photosynthesis through absorbing light energy and transferring the energy to a reaction center. Osmium
metal complexes also absorb light and can be used in energy transfer reactions. Having recently published
studies on the simplest osmium-porphyrin dyad, the first examples of an osmium attached through
coordination directly to the porphyrin periphery, we are expanding this study to include modified
porphyrins and modified osmium complexes. By joining together these two moieties, the ability of the
complexes to absorb light and transfer the energy can be modified. We have found that the osmium portion
absorbs the light and transfers the energy to the porphyrin fragment. A new series of osmium-porphyrin
compounds are being synthesized and studied to explore their light harvesting capabilities. These
alterations change the light absorbing and emitting properties of the complexes and will affect the energy
transfer reactions that may occur.
R
R
N
N
M
2+
N
N
OC
N
N
Os N
N N
M = H 2 or Z n
R = CH 3
O Me
F
CN
R
ELECTROCHEMICAL STUDY OF RHODIUM(III) POLYPYRIDYL COMPLEXES.
Christopher Emmel and Elise G. Megehee, Department of Chemistry, St. John’s University,
Jamaica, NY 11439.
The polypyridyl rhodium(III) complexes that have been studied are of interest as possible photochemical or
electrochemical catalysts, as emissive DNA labels, as probes of DNA and protein structure, and as reagents
for the photochemical cleavage of DNA. Over the past year many new rhodium complexes have been
synthesized in our research group. Along with 1H NMR, 13C NMR, and elemental analysis we have begun
to investigate the electrochemical properties of these complexes. While doing the cyclic voltammetric
analysis of these complexes, we had to deal with several issues such as light sensitivity and proper solvent
selection. The cyclic voltammetry data now being obtained is providing good basis for characterization of
these complexes by electrochemical means.
32
CHARACTERIZATION OF NEW MIXED LIGAND RHODIUM(III) COMPLEXES.
Daniel Amarante and Elise G. Megehee, Department of Chemistry, St. John'
s University,
Jamaica, NY 11439.
Known rhodium(III) polypyridyl complexes exhibit absorption of ultraviolet to visible light and emission
of visible to near infrared light. The few known examples of mixed ligand complexes were synthesized in
very low yields by a wide variety of methods. We have developed a general high yield synthetic strategy
for synthesizing mixed ligand polypyridyl complexes of rhodium (III). To date we have synthesized
fourteen rhodium complexes of the form [Rh(bpy)2(NN)](PF6)3 (where bpy = 2,2'
-bipyridine, NN = 2,2'
bipyrdine, 1,10-phenantroline and their derivatives) using cis-[Rh(bpy)2(OTf)2](OTf) as the starting
material. We have studied these compounds by 1H-NMR, 13C-NMR, UV/Vis, and Cyclic Voltammetry.
Synthesis and characterization will be discussed.
3+
+
H3 C
N
N
N
Rh
N
OTf
OTf
CH3
N
N
EtOH
∆
N
N
N
Rh
N
CH3
N
N
CH3
THE EFFECT OF PARTICLE SIZES AND COMPOSITION VARIATIONS ON
RATE OF APATITE FORM IN SOL-GEL DERIVED BIOGLASS. Olajide Alawode,
Safiyyah Hossain, Dr. Adeniji, Dr. Aderemi Oki. Department of Chemistry & Biochemistry,
Long Island University, Brooklyn, NY 11201
The bioactive glass with composition SiO2-P2O5-CaO-ZnO has recently being synthesized by sol-gel
processing, and it bioactivity has been tested in simulated body fluid and in bone cells. This composition
of Bioglass is able to form biologic apatite in SBF, an indication of bone bonding ability. In addition,
invitro experiments using human fetal osteoblastic cells hfob1.19 showed that this composition of Bioglass
stimulates early bone cell differentiation. The present work reports how variable such as particle size and
percent composition of the materials affects the bioactivity in SBF. Bioglass materials of different
particle size were analyze using Fourier transform infra-red spectroscopy (FTIR) , Powder X-ray
diffraction spectroscopy (XRD) and differential thermal analyzer (DTA) to characterized this material, and
determine the effect on apatite formation. The effect of particle size on material dissolution and solution
pH variation will also be presented.
HYDROGEN BONDING COUNTERIONS IN [4Fe-4S] CLUSTERS OF
FERRODOXIN MODEL COMPLEXES Cara Roche, Marc. A. Walters Department of
Chemistry, New York University, New York, NY 10003
A series of Fe4S4 complexes, (CTA)2[Fe4S4 L4], (L = Cl, SPh, St-butyl), CTA = {(CH)3NCH2CONH2 }+
was synthesized to investigate hydrogen bonding of the counterion to the inorganic sulfur of the clusters.
The clusters were synthesized to mimic biological Fe4S4 clusters in the peptide environments of
ferrodoxins. The amide group of CTA serves as a hydrogen bond donor much like the peptide amide
groups of the proteins. H-NMR, IR, and UV-vis data were collected on each compound in the series and xray crystallographic data was obtained on the complex with the tert-butyl thiolate terminal ligands. The
presence of hydrogen bonding in the samples is suggested by the IR data in the 3000 cm-1 region. Crystal
structure data confirms the presence of hydrogen bonding interactions between amide and both inorganic
and thiolate sulfur atoms. This is the first example of a model complex of ferrodoxin that displays hydrogen
bonding between the counterion and the inorganic sulfur of the a [Fe4S4 ]+2 cluster.
33
TETRACHLOROMETALLATES OF 1,4-DIAZABICYCLO[2.2.2]OCTANE. Ada
Gjyrezi and Raifah Kabbani. Department of Chemistry and Physical Sciences, New York,
NY 10038.
This project involves the preparation of organic-inorganic composites crystals. These materials offer the
potential of being used as light or electrical sensors due to their magnetic and electrical properties. Long
chain ammonium derivatives of 1,4 diazabicyclo[2.2.2]octane (DABCO) have been prepared and
complexed with PdCl42-, ZnBr42- and CuBr42- (below). The organic substituent has been varied in length in
order to study the effect of the organic chain on the elasticity and solubility of the complexes. Compounds
of the general formula M2(DABCO)2R2X6 where [M=Cu, Pd, Ni, Zn; R=C12H25, C16H33; X= Cl, Br] have
been synthesized. The resulting complexes were analyzed using elemental analysis, UV-vis, and NMR.
Synthesis, structural characterization of the resulting compounds and the interaction between the layers will
be presented.
Br
N
N
Br
M
M
Br
Br
N
Br
Br
N
FINE TUNING LIGANDS FOR USE IN HYDROFORMYLATION REACTIONS
WITHIN IONIC LIQUIDS., Nawras Harsouni, Christi Gandham, Jyothsna Singavarapu,
Richard J. Rosso, Department of Chemistry, St. John’s University, Jamaica, NY 11439
Catalytic reactions are an important part of organometallic chemistry. These reactions are especially useful
if they can occur under both mild (low pressure and temperature) and environmentally safe conditions
while still retaining high product selectivity. Ionic liquids possess many of these properties and are an
attractive alternative for use as solvents within biphasic catalytic reactions. We are currently developing
synthetic methods to produce a variety of diphenylalkylphosphine and triphenylphosphine derivatives with
different carbon chain lengths between the phosphorus atom and a charged moiety to act as ligands for
rhodium catalyzed hydrogenation and hydroformylation reactions within ionic liquids media. Examples of
the effect chain length have on the solubility of the catalyst, reaction rate, and product distribution will be
investigated.
THE SYNTHESIS OF NOVEL COBALT COMPEXES CONTAINING TRIPOD
LIGANDS AS MODELS FOR POTENTIAL HYDROFORMYLATION CATALYSTS.
Seda Bilginer and Stephen Anderson, School of Theoretical and Applied Sciences, Ramapo
College of New Jersey, Mahwah, NJ 07430
The hydroformylation of alkenes is an important industrial process in which CO and H2 adds across the
carbon-carbon double bond producing aldehydes. For unsymmetrical alkenes, the reaction yields either a
straight-chain or branched product. A cobalt or rhodium catalyst is used along with a vast excess of a
phosphine ligand in order to increase the yield of linear product. The goal of this project is to synthesize
cobalt complexes containing the tripod ligands hydrotris(pyrazol-yl) borate (Tp) and TRIPHOS. These
‘scorpionate’ ligands contain potential free-arms which could have the same influence on the catalytic
reaction as adding excess phosphine. Their effectiveness as hydrofrylation catalysts will then be
investigated.
THE SYNTHESIS OF Di-ACYL COMPLEXES OF IRON AND TUNGSTEN AS
ISOELECTRONIC MODELS OF β -DIKETONATES . Zafar Iqbal and Stephen
Anderson, School of Theoretical and Applied Sciences, Ramapo College of New Jersey,
Mahwah, NJ 07430
The removal of a hydrogen atom from 2,4-pentanedione yields the β-diketonate known as acetacetonate
(acac). This reagent has the ability to act as a bidentate chelate ligand and forms metal acetylacetonate
complexes of the type [M(acac)3]n+.These are often used as MOCVD precursors to inorganic materials. The
goal of this project is to synthesize a range of transition metal di-acyl complexes of the type
[M{C(O)R}2(CO)n], and investigate the similarity between organic β-diketonates and these
metalladiketonates.
34
NANO AND SURFACE CHEMISTRY
NANOWIRES OF TUNGSTEN AND MOLYBDENUM OXIDE PREPARED BY
ELECTROSPINNING Katarzyna M. Sawicka, M. Karadge, A. K. Prasad and P. I. Gouma
Material Science and Engineering Department, St. John'
s University, 8000 Utopia Parkway,
Jamaica, NY 11439
With the increasing demand for nanotechnology the electrospinning technique is an emerging fabrication
method to produce nanofibers of polymers or composite materials. One dimensional nanoscaled materials
are of interest due to their unique electronic, magnetic and mechanical properties. The objective of this
experiment is to produce metal oxide nanowires, by employing the electrospinning method followed by
oxidation, thermal evaporation. This was achieved by combining mixtures of metal oxide sol gels and
polymer solutions together. Polyvinylpyrrolidone with an average molecular weight of 1,300,000 was the
polymer chosen in order to avoid formation of beads, the most frequent artifact of electrospinning.
Tungsten trioxide and molybdenum trioxide were chosen due to their specificity to the detection of
ammonia and nitrogen dioxide gases respectively. The aim of this experiment was to obtain metal oxide
nanowires having high surface areas for improved gas detection sensitivity therefore composite PVP-metal
oxide nanofibers were produced. As confirmed by the TEM and SEM microscopy analysis carried out on
the as received nanocomposite, the metal oxide remained inside the polymer nanofibers. The nonwoven
mats are characterized by large surface area and small pore sizes. To obtain self supported metal oxide
nanowires specific heat treatments were conducted. These include multistep processes of heat treating in
vacuum, inert, or reducing atmospheres to control and optimize the morphology and aspect ratio of the
metal oxide nanowires. This novel nanofabrication process is critical in the synthesis of sensors, smart
textiles, nanobatteries, biomaterials.
SYNTHESIS AND CHARACTERIZATION OF VARIOUS CDA-Cl REVERSE
MICELLES. Pamela Tadross, Marc Walters, Department of Chemistry, New York
University, New York, NY, 10003
Reverse micelles allow for unique microenvironments for diverse applications that include catalysis and
nanoparticle synthesis. Herein we present the results of novel, initial research on a hydrogen bonding
congener of a common surfactant, cetyltrimethylammonium bromide (CTAB). The substitution of one of
CTAB’s N-methyl groups with an acetamide group results in a surfactant, CDA-Cl, whose head group is
well suited for hydrogen bonding. This surfactant and its reverse micelle phase has been characterized by
NMR. The hydrodynamic radius of the particles has been determined by conductivity and dynamic light
scattering and a phase diagram has been constructed for the CDA-Cl/CHCl3/H2O ternary system. The
metal complexes [FeCl4]- and [Fe(CN)6]3- have been incorporated within the core of the CTAB and CDACl reverse micelles and their properties studied. NMR, UV-Visible spectroscopy and X-Ray
Crystallography were employed in characterization of these systems.
CDA-Cl
35
SELECTIVE MODIFICATION OF β -CYCLODEXTRIN FOR USE AS A
SUPRAMOLECULAR SCAFFOLD. Jason A. Estrada, Zachary E. Katsamanis and
Nancy S. Goroff, Department of Chemistry, SUNY Stony Brook, Stony Brook, NY 117943400
A “Buckybelt” (1) is a cylindrical, carbon-rich, aromatic molecule with a structure similar to the equatorial
region of the infamous “buckyball” C60. The buckybelts are predicted to have interesting and potentially
useful properties, such as the ability to act as an organic semiconductor. The focus of our research is to
synthesize a buckybelt using a scaffolding strategy based on the rigid cylindrical shape and well-known
chemistry of cyclodextrin. The research presented here involves our efforts to modify cyclodextrin
chemistry to allow attachment of our designed aromatic groups that will be used as the building blocks of
the belt. The two faces of the cyclodextrin cylinder have different reactivities, and we exploit this subtle
difference to treat each face separately. We have also studied the attachment of our designed aromatic
groups using several different attachment strategies.
R
R R
R
R RR RR R R
R
36
ORGANIC CHEMISTRY
TOTAL SYNTHESIS OF THE SESQUITERPENOID YLANGENE
Julia Christodoulou and Sasan Karimi, Department of Chemistry and Biochemistry, Queens
College, Flushing NY 11367 and Department of Chemistry, Queensborough Community
College, Bayside NY 11364
Ylangene, a naturally occurring tricyclic sesquiterpene, was obtained from the ancient plant, schizandra
chinensis, and has been used for centuries throughout the Far East, China, and Japan to treat fatigue and
exhaustion. The structural assignment of ylangene, as well as its isomeric hydrocarbon copaene, was
proposed in 1965 and its first total synthesis was achieved by Heathcock in 1967. We propose to synthesize
ylangene, based on a methodology developed in our lab (involving an intramolecular cyclization reaction)
towards the synthesis of sativene and longifolene.
Ylangene
CONFORMATION OF THE SESQUITERPENOID PRECURSOR OF
LONGIFOLENE USING NMR SPECTROSCOPY. Richard Gastel, Sasan Karimi, and
Gopal Subramaniam, Department of Chemistry, Queensborough Community College,
Bayside, NY 11364 & Department of Chemistry & Biochemistry, Queens College, Flushing,
NY 11367
We recently synthesized 3,3,7-trimethyltricyclo[5.4.0.02,9]undecan-8-one (1), a sesquiterpenoid precursor
of longifolene. Assignment of 1H and 13C NMR signals were achieved with a variety of 1D and 2D NMR
techniques. The methylene protons at C4, C5, C6, C10, and C11 as well as the methyl groups at C3 were
nonequivalent and their stereospecific assignments were done by 2D NOESY. Conformational analysis was
carried out using the Guassian-03W program and the lowest energy structure was correlated with
experimental observations.
13
14
4
3
2
11
10
1
9
5
6
7
12
8
1
O
FREE RADICAL CHLORINATION OF 1o, 2o, AND 3o BENZYLIC HYDROGENS.
Shinsung Lee, Sasan Karimi, David Locke, Gopal Subramaniam, Paris Svoronos,
Department of Chemistry, Queens College and Queensborough Community College of
CUNY
The free radical chlorination products of several alkyl aromatic compounds containing primary, secondary,
and tertiary hydrogens have been investigated and the relative reactivity ratios for the various hydrogens
are reported.
Sulfuryl chloride and N-chlorosuccinimide were used as the source for the chlorine radicals with AIBN and
benzoyl peroxide as the radical initiators. The final objective is to obtain the relative reactivity ratios
for3o:2o:1o benzylic hydrogens and compare them to the corresponding ratios of aliphatic 3o:2o:1o.
37
SELECTIVE DEPROTECTION OF D-6,3-GLUCURUNOLACTONE ESTERS
Halimatu Sadiya Mohammed, Therese Soosairaj,, Panayiotis Meleties, Department of
Chemistry, Bronx Community College of the City University of New York, E. 181 St. &
University Ave., Bronx, NY 10453
Treatment of protected carbohydrate derivatives with a solution of I2 in methanol is reported to be a very
efficient method to selectively deprotect the substrate. Recent examples include cleavage of isopropylidene
acetals, thioacetals, silylethers and trityl ethers. Other applications of I2 in solvents other than methanol
include the conversion of alcohols to iodoalkanes. Application of the I2/ methanol reagent on
isopropylidene esters of D-6,3-glucurunolactone lead to a mixture of products. Cleavage of the 1,2isopropylidene group yielded the predicted methyl glycoside derivatives. Concomitant ester cleavage was
also observed. The carbohydrate ester cleavage is a result of a transesterification reaction with methanol
catalyzed by I2.
THE DIELS-ALDER ADDUCTS OF PERIODOBUTATRIENE AND
PERBROMOBUTATRIENE Obianauju C. Nduka and Nancy S. Goroff,
Department of Chemistry, Stony Brook University, Stony Brook, NY 11794
Our group has developed the first synthesis of tetraiodobutatriene (C4I4) and tetrabromobutatriene
(C4Br4). C4I4 is synthesized from diodobutadiyne and iodine in hexane at room temperature. C4Br4 is made
by reaction of dibromobutadiyne and bromine at -20° C. The chemical properties of both cumulenes are
still being explored. Three different Diels-Alder reactions were attempted using C4I4. The first reaction of
C4I4 with furan was unsuccessful, resulting in isolation only of the starting materials. We have also studied
the Diels-Alder reactions of 1,3-cyclopentadiene and 1,3-cyclophexadiene with C4I4, both computationally
and experimentally. We are still determining the course of each of theses reactions, but the expected
products are compounds 1 and 2, respectively.
In addition, we have analyzed the possible products from the Suzuki reaction of 3 and phenyl
boronic acid. We have calculated the 1H and 13C NMR spectra for each proposed structure, using both
GIAO (B3LYP/6-31G*) and IGLO (BP91/IGLOII) methods. Comparison of these results with
experimental data has helped determine the course of this reaction, which leads to compound 5 instead of
the expected 4.
I
I
Br
O
I
I
I
Br
Br
I
I
Br
I
1
2
3
Br
Br
Br
Br
Br
Br
Ph
Br
HO
Ph
4
5
38
BOROHYDRIDE REDUCTION OF QUINOXALINES
Elena Savrides and Dr. Terrence Gavin, Iona College.
Quinoxalines 1a (R = phenyl; R’= H) and 1b (R = R’= phenyl) were reduced to their 1,2,3,4-tetrahydro
derivatives, 2a and 2b, with sodium borohydride in acetic acid. Subsequent reaction of 2a with acetic
anhydride resulted in a regioselective acylation to give compound 3a, 1,2,3,4-tetrahydro-1-acetyl-3phenylquinoxaline.
N
R '
N
R
N a B4 H
A c O H
1
C O C
3 H
H
N
R '
N
H
R
A 2cO
2
N
R '
N
H
R
3
EFFICIENT PREPARATION OF ACYCLIC AMIDINIUM SALTS BY
ORTHOESTER EXCHANGE AND AMIDINIUM SALT TRANSAMINATION.
Marinda M. Rivera, Shahrokh Saba, Adeline Kojtari, Peter D’Amico, Dana Canuso, and
Moses K. Kaloustian, Department of Chemistry, Fordham University, Bronx, New York
10458
A series of symmetrical and unsymmetrical acyclic amidinium hexafluorophosphates were prepared in
good yields. Symmetrical N,N’-dialkyl-substituded formamidinium salts were produced by direct reaction
of triethyl orthoformate with two equivalents of a 1o amine in the presence of ammonium
hexafluorophosphate. N,N,N’-Trialkyl- and N,N,N’,N’-tetraalkyl-substituted formamidinium salts were
prepared by transamination of N,N-disubstituted formamidinium hexafluorophosphates using 1o and 2o
amines, respectively.
E tO
O Et
O Et
R HN
N H 4 PF 6
2 R- NH 2
+
N HR
+
PF 6 -
H
R 2N
+
N H2
PF 6 -
+
R
H (R ')
NH
R 2N
H(R ')
N
+
R
PF 6
-
SYNTHESIS OF PHOSPHINES FROM PYRILIUM SALTS AND TETRAKIS
(HYDROXYMETHYL) PHOSPHONIUM CHLORIDE, Kelly Daggett, Dr. James
McCullagh, Manhattan College, Riverdale NY, 10471
The purpose of our project is to synthesize Phosphinine (phosphabenzene) ligands (3) for transition metal
catalysis. One method of synthesis involves pyrilium salts (1) which can be made from cheap and readily
available precursors. Traditional this is done by reaction of Tris (hydroxymethyl) phosphine with pyrilium
salts. However; this phosphine is very expensive and not commercially available in a highly pure form. In
this work we are investigating using the cheap and readily available Tetrakis (hydroxymethyl)
Phosphonium chloride salt (2) as an alternative to Tris (hydroxymethyl) phosphine in the synthesis of
Phosphinines (Phosphabenzenes) (3).
(2)
R
R
OH
HO
O
P
XR
O
R
HO
+
OH
BA SE
P
(3)
39
C
H
R
(1)
4
R
H
ACCIDENTAL SYNTHESIS OF BENZAZEPINES: PREPARATION OF 2,4DIARYL-3H-1-BENZAZEPINES Myra Cheng, Shaan Alli, Richard Leung, Michelle
Washington, Keith Ramig, Department of Natural Sciences, Baruch College, CUNY, 17
Lexington Ave., New York, NY 10010; Linas V. Kudzma, Baxter Healthcare Corporation,
Anesthesia and Critical Care, 95 Spring St., New Providence, NJ 07974
Treatment of aryl methyl ketones with 2-fluoroaniline unexpectedly gives 1-benazepine derivatives. The
scope and limitations of the synthesis will be presented, along with some speculations about the
mechanism.
A r
N H2
O
F
+
A r
N
H O T s
A r
2 ,4 - d ia r y l- 3
b e n z a z e p in e s
NEW STRATEGY FOR THE SYNTHESIS OF ISOFLURANE ENANTIOMERS
Shaan Alli, Myra Cheng, Keith Ramig, Department of Natural Sciences, Baruch College,
CUNY, 17 Lexington Ave., New York, NY 10010
The racemic form of isoflurane is an important inhaled anesthetic. It has been shown that its enantiomers
have differing potencies in rodents, making a practical stereoselective synthesis of isoflurane desirable. We
will present our progress toward this goal. The enol ether 2 is easily prepared from fluoroether 1 by
treatment with sodium methoxide. Addition of chlorine across the double bond gives dichloroether 3,
which gives ester 4 after brief acidic hydrolysis. Saponification of the ester gives the key chiral racemic
acid 5. We have found that the potassium salt of the racemic form of acid 5 decarboxylates when heated in
a protic solvent, giving racemic isoflurane. Progress is being made in the enantiomeric resolution of acid 5,
the next step being its stereoselective decarboxylation to give isoflurane enantiomers. If this is achieved,
then a fully stereoselective synthesis of isoflurane, including stereoselective preparation of acid 5, will be
the ultimate goal.
F2H C O
C F3
F3C
OMe
N a O M e F2H C O
F3C
1
C 2l
F2H C O
OMe
F3C
OMe
Cl
OMe
2
O
F2H C O
F3C
OMe
Cl
4
L iO H
Cl
H3 O+
3
O
F2H C O
F3C
OH
Cl
5
KOH
F2H C O
∆
F3C
H
Cl
Is o f lu ra n e
A GENERAL HIGH YIELDING SYNTHESIS OF ISOCYANIDES, Kathryn Bardsley
and Victor Cesare, Department of Chemistry, St. John'
s University, Jamaica, NY 11439.
A new synthesis of isocyanides (isonitriles), by means of reacting various primary amines with
dichlorocarbene (synthesized in situ from sodium hydride and chloroform) and employing a catalytic
amount of 15-crown-5 ether, has provided various isonitriles in improved yields. This method avoids the
use of phosgene as described in a previous synthesis.
40
NEW POLYPHOSPHORUS AMIDE ANALOGUES. Zeba Izhar, Chris Massone, Robert
Engel, Department of Chemistry, Queensborough Community College, Bayside, NY 11364,
and Department of Chemistry, Queens College, Flushing, NY 11365.
Polyphosphorus amide analogues are amides whose carbon and nitrogen atoms have been replaced by
phosphorus atoms. Previous studies in our laboratory have focused upon the addition of mono-, bi-, and
tridentate phosphorus ligands to Diphenyl chlorophosphate and Diethyl chlorophosphate, leading to the
replacement of the carbonyl group with a phosphoryl group and the replacement of the amine group with a
phosphonium group. In an extension to this exploratory work, our current project looks at the addition of
mono-, bi-, and tridentate phosphorus ligands to Di-o-tolyl chlorophosphate (1) and Di-p-tolyl
chlorophosphate (2). Each compound synthesized in this study has been characterized by 1H, 13C, and 31P
NMR.
CH
O
3
O
O
O
P
Cl
H 3C
P
Cl
O
O
H 3C
CH
1
3
2
NEW HEXACOORDINATED PHOSPHORUS COMPOUNDS. Jennifer West, Chris
Massone, Robert Engel, Department of Chemistry, Queensborough Community College,
Bayside, NY 11364, and Department of Chemistry, Queens College, Flushing, NY 11365.
Hexacoordinated phosphorus compounds are an intriguing class of compounds characterized by a
negatively charged phosphorus center. Previous studies in our laboratory have focused upon the addition
of mono- and bidentate nitrogen and phosphorus ligands to two pentacoordinated phosphorus precursors
derived from the reactions of phosphorus pentachloride with catechol and with 2,3-dihydroxynaphthalene.
In this new part of our exploratory research we focus upon the addition of mono- and bidentate nitrogen
and phosphorus ligands to two different pentacoordinated phosphorus precursors 1 and 2. Each compound
synthesized in this study has been characterized by 1H, 13C, and 31P NMR.
Cl
Cl
O
O
O
O
O
O
O
P
P
O
2
1
PROPOSED SYNTHESIS OF 1-T-BUTYL-3-(4-NITROPHENYL) AZIRIDINONE
Nadege Beaulieu1; Ralph Stephani2; Luis A.Vargas1. 1Department of Chemistry,
Queensborough Community College, Bayside, New York. 2 Department of Pharmaceutical
Science, St. John’s University, Jamaica, New York.
1-t-butyl-3-(4-nitrophenyl)aziridinone was synthesized from p-nitrophenyl acetic acid by its conversion to
the corresponding acyl halide (I, via SOCl2), the -bromoacyl halide (II, via NBS), the amide (III) and
conversion to the lactam (IV) with NaH/base/crown ether, as seen below. The objective is to react (IV) with
P(OSi(CH3)3) 3 (TMSP) and study the reaction products .
Br
R
R
Br
COCl
COCl
COOH
I
R
CONHR'
II
R
III
O
CH3
R=
NO2
R'=
CH3
CH3
N
R
41
IV
R'
SYNTHESIS OF 1, 3-DI-T-TERT-BUTYLAZIRIDINONE (2) AND CLEAVAGE
WITH TRIS(TRIMETHYLSILYL)PHOSPHITE (TMSP) Jiang Yang1; Ralph Stephani2;
Luis A. Vargas1. 1Department of Chemistry, Queensborough Community College, Bayside,
New York. 2 Department of Pharmaceutical Science, St. John’s University, Jamaica, New
York.
1,3-Di-t-butylaziridinone (IV) was synthesized from 3,3-dimethylbutanoic acid by its conversion to the
corresponding acyl halide (I, via SOCl2), the -bromoacyl halide (II, via NBS), the amide (III) and
conversion to the lactam (IV) with NaH/base/crown ether, as seen below:
Br
COOH
R
R
Br
COCl
COCl
I
R
CONHR'
II
R
O
CH3
R = R'=
III
CH3
CH3
N
R
R'
IV
Cleavage of (IV) with P(OSi(CH3)3) 3 (TMSP) yielded the silylated t-butylphosphonic acid
(CH3)3CP(O)(OSi(CH3)3 )(OH) and t-butyl acetamide as evidenced by GC/MS.
SYNTHESIS OF 1-(1-ADAMANTYL)-3-T-BUTYLAZIRIDINONE AND CLEAVAGE
WITH TRIS(TRIMETHYLSILYL)PHOSPHITE (TMSP) Shazim Mobin1, Ralph
Stephani2, Luis Vargas A.1. 1Department of Chemistry, Queensborough Community College,
Bayside, New York, 2 Department of Pharmaceutical Science, St. John’s University, Jamaica,
New York.
1-(1-Adamantyl)-3-t-butylaziridinone was synthesized from 3,3-dimethylbutanoic acid by its conversion to
the corresponding acyl halide (I, via SOCl2), the -bromoacyl halide (II, via NBS), the amide (III) and
conversion to the lactam (IV) with NaH/base/crown ether, as seen below
Br
Br
COCl
COCl
COOH
R
R
I
R
CONHR'
II
R
III
O
CH3
R=
CH3
R'=
N
CH3
R
IV
Cleavage of (IV) with P(OSi(CH3)3)3 (TMSP) yielded the silylated t-butylphosphonic acid
(CH3)3CP(O)(OSi(CH3)3 )(OH) and adamantyl acetamide as evidenced by GC/MS.
42
R'
SYNTHESIS OF ARYL-5-(5-PHENYLPENTYL) DERIVATIVES VIA ONE STEP
PROCESS. Daffadil Williams and Kwesi Amoa, Department of Physical, Environmental,
and Computer Sciences, Brooklyn, New York 11225
Aryl-5-(5-phenylpentyl) derivatives can be derived from 1,4-pentadiene-3-one type system. However, to
cause this transformation, a three-step process is required. Preliminary results have shown that treatment of
a pentadiene-3-one type system under acidic conditions produced the aryl-5-(5-phenylpentyl) derivatives
via one step. Despite this promising result, this reaction produced partially reduced compounds. This work
further explore the chemistry of this system and reports and an optimized procedure for this
transformation.
R1
R
H2/Cat. H+
R2
R3
R1
O
R2
R3
R4
R
R4
SELECTIVE DEPROTECTION OF D-6,3-GLUCURUNOLACTONE ESTERS
Therese Soosairaj, Halimatu Sadiya Mohammed, Panayiotis Meleties, Department of
Chemistry, Bronx Community College of the City University of New York, E. 181 St. &
University Ave., Bronx, NY 10453
Treatment of protected carbohydrate derivatives with a solution of I2 in methanol is reported to be a very
efficient method to selectively deprotect the substrate. Recent examples include cleavage of isopropylidene
acetals, thioacetals, silylethers and trityl ethers. Other applications of I2 in solvents other than methanol
include the conversion of alcohols to iodoalkanes. Application of the I2/ methanol reagent on
isopropylidene esters of D-6,3-glucurunolactone lead to a mixture of products. Cleavage of the 1,2isopropylidene group yielded the predicted methyl glycoside derivatives. Concomitant ester cleavage was
also observed. The carbohydrate ester cleavage is a result of a transesterification reaction with methanol
catalyzed by I2.
SYNTHESIS OF PEGYLATED INSULIN FRAGMENTS: MODEL COMPOUNDS
FOR SITE-SPECIFIC PEGYLATION OF INSULIN. Ashley Carbone and Arthur M.
Felix, Ramapo College of New Jersey, Theoretical and Applied Sciences, Mahwah, NJ 07430
Pegylation involves the attachment of one or more flexible strands of poly(ethyleneglycol) (PEG) to a
functional group present in the side-chain of a peptide or protein. Important advantages have been observed
in the resultant pegylated products including improved biological activity and several pegylated
pharmaceuticals have been marketed in the last few years. However, pegylation of these products is
introduced by chemical conjugation to functional groups on the protein. Since it is difficult to control such
chemical coupling reactions the resultant products are indiscriminately pegylated. The site of pegylation is
crucial and if it is carefully controlled, the therapeutic will have improved biological properties. Research is
being carried out in our laboratory to develop conditions for the site-specific pegylation of insulin using
enzyme catalysis for the attachment of PEG to the COOH-terminus of the beta chain of insulin. In this first
stage of the research we have prepared H-Pro-Lys-Thr-PEG, which corresponds to residues 28-30 of the
beta chain of insulin that is pegylated at the COOH-terminus (a site that is removed from the
pharmacophoric region of insulin). This model compound will be used as an analytical tool for our next
stage of research, which involves the enzyme catalyzed pegylation of H-Pro-Lys-OH with H-Thr-PEG.
43
BIS- AND TRIS-BRANCHED PEGYLATING REAGENTS: CONJUGATION TO
COOH-TERMINAL AND NH2- TERMINAL PEPTIDES. Rajintha M. Bandaranayake
and Arthur M. Felix, School of Theoretical and Applied Sciences, Ramapo College of New
Jersey, Mahwah, NJ 07430
Pegylation is a process by which functionalized, linear poly(ethylene glycol) (PEG) polymer chains are
attached to biologically important molecules. Many PEG coupled biomolecules are reported to have
increased plasma half-lives as well as improved solubility, increased resistance to proteolysis and reduced
toxicity and immunogenicity. It has also been reported that branched pegylating reagents further enhance
these properties when compared to linear pegylating reagents. In previous work conducted in our laboratory
we have developed a solution-phase process to synthesize bis- and tris-branched pegylating reagents which
contain a free NH2-terminus. In this procedure, PEG units were introduced stepwise to orthogonally
protected lysine and glutamic acid to generate mono- and bis-pegylating reagents. These pegylating
reagents were then coupled to generate the tris-pegylating reagent. The novel branched bis- and trispegylating reagents were then successfully coupled to the COOH- terminus of the model penta-peptide,
Fmoc-cyclo1,5-Lys-Tyr-(tBu)-Leu-Asn-Asp-OH. Using similar methods we have now successfully
synthesized bis- and tris-branched pegylating reagents which contain a free COOH-terminus. These novel
bis- and tris-branched pegylating reagents have been coupled to the NH2-terminus of the model peptide,
H2N-Leu-Lys(Boc)-Lys(Boc)-Gly-Gly-Thr(tBu)-CONH2 in order to demonstrate the use of these novel
pegylating reagents.
ELECTROCHEMICAL OXIDATIONS OF PROTECTED PYRROLIDINES AND
PROLINE DERIVATIVES Cara Boutte, Dr. S.E. Watson, Dept. of Chemistry, Long Island
University.
The ultimate goal of this project is the synthesis of a 7,5 bicyclic lactam using electrochemical oxidation as
a key step. This molecule is designed to be a potential inhibitor of farnesyl transferase, a key enzyme in
the cell division signal transduction pathway and therefore a potential anti-tumor agent. The bicylcic
lactam is designed to function as a mimic of a beta-turn. Anodic oxidations of pyrrolidine and proline
derivatives were studied using methanol as the solvent. The ultimate goal is to use the N-allyl glycine
proline methyl ester derivative. If it can be methoxylated at the alpha position, treatment with a Lewis acid
can be used to close the ring to form the 7,5-bicyclic system. This method would be more efficient than
current synthetic routes.
CHE RESEARCH ABSTRACTS: QUANTIFYING THE CONTRIBUTION OF
DIFFERENT SUBSTITUENTS TO 1, 3-ALLYLIC STRAIN. Nan Wang Department of
Chemistry, SUNY-StonyBrook, New York, NY 11794-3400
Controlling molecular conformations and stereochemistry is very important for Chemistry experiments and
research. For instance, we know that the axial and equatorial substitutions play important roles in the
molecular conformations of cyclohexanes; and thus, they influence the stabilities of cyclohexane
conformations. Similarly, the 1, 3-allylic interactions also have great impacts on the stabilities of
molecular conformations. Experiments have shown that they can in some cases have a greater magnitude
than 1,3-diaxial interactions of cyclohexanes. However, the 1,3-allylic interactions are less recognized.
The goal of my research is to figure out the allylic energy changes or allylic strains for different
substituented allylic molecules.
Allylic molelule has a common structure, which is the CH2=CHCH2−group.
For my research purpose, I will use the structure of CH2X CH CHY for the allylic molecules. Therefore,
if I choose different substituents X and Y to the allylic molecule, I would expect to see changes in
conformational energies. The substituents X and Y I use in my research are –H, -CH3, -F, -Cl, -NH2, -OH,
and -SH groups. In addition, for an allylic molecule with a specific X and Y substituents, I will examine
the energy difference between its cis and trans conformations. Among these different allylic
conformations, I will find out the most stable conformation for each allylic molecule with a specific X and
Y substituents, and compare the stabilities of different substituented allylic molecules with each other.
44
POLYMER CHEMISTRY
CHARACTERIZATION OF NEW TYPES OF ETHER CONTAINING IONIC
LIQUIDS. Annu Ipe,1Carolyn Spence,1 Delroy Coleman,2 Wadson Miranda,2 Robert Engel2
and Sharon Lall-Ramnarine.1 1Department of Chemistry, Queensborough Community
College, CUNY, Bayside, NY 11364. 2Department of Chemistry and Biochemistry, Queens
College, CUNY, Flushing, NY 11367
Ionic liquids are being investigated as solvent alternatives in a myriad of applications. In order to fully
explore the potential of these new species, knowledge of their physical and chemical properties is
necessary. Prior reports from this laboratory have focused on the preparation and characterization of new
types of polyammonium ionic liquids, where the anion was either phosphate (PO43-) or
bis(trifluoromethyl)sulfonylimide (NTf2). We report here on the characterization of yet another category of
ionic liquids, where ether functionalities are incorporated into the polyammonium cation. This has been
reported by others and observed by us as lowering the viscosity of the resulting liquids. The associated
anions of these new species are either phosphate or halide. The structures of these new species have been
confirmed by 1H, 13C and 31P NMR. The water content of liquids were determined by Karl Fischer Titration
and preliminary results of their conductivity are reported.
SYNTHESIS OF NEW TYPES OF ETHER CONTAINING IONIC LIQUIDS. Carolyn
Spence,1 Annu Ipe,1 Carolyn Spence,1 Delroy Coleman,2 Wadson Miranda,2 Robert Engel2
and Sharon Lall-Ramnarine.1 1Department of Chemistry, Queensborough Community
College, CUNY, Bayside, NY 11364. 2Department of Chemistry and Biochemistry, Queens
College, CUNY, Flushing, NY 11367
Ionic liquids continue to attract widespread attention as new and intriguing liquid salts for use as alternative
solvents. Prior reports from this laboratory have focused on the preparation of new types of polyammonium
ionic liquids, where the anion was either phosphate (PO43-) or bis(trifluoromethyl)sulfonylimide (NTf2). We
report here on the preparation of yet another category of ionic liquids, where ether functionalities are
incorporated into the polyammonium cation. This has been reported by others and observed by us as
lowering the viscosity of the resulting liquids. The associated anions of these new species are either
phosphate or halide. The structures of new species have been confirmed by 1H, 13C and 31P NMR.
PREPARATION AND INVESTIGATION OF POLYAMMONIUM HYDROGEL
AGAROSE. Teshell K. Greene, Renee Carrington, Nadia Hussain, JaimeLee I. Cohen,
Department of Chemistry and Physical Sciences, PACE University, New York, NY 10038
Agarose is a polysaccharide (Figure 1), and it usually exhibits essentially the same common properties
typical of polymeric substances. Past efforts of our laboratory include the modification of carbohydrate,
proteinaceous, alginate, and chitosan surfaces to render those materials antimicrobial. Our current work is
directed toward the modification of agarose by the attachment of a series of polyammonium organic salts.
The modified agaraose retains its hydrogel characteristics; has demonstrated antimicrobial activity just as
the other surfaces our group has been successful at derivatizing. The physical and antibacterial/antifungal
characteristics are currently being investigated. This polyammonium agarose forms a new surface and its
utility is being sought.
+
( C 2H)n C H
3
N
O H
+
N
O
O
O
O
O
O
O H
O H
Figure 1 – Modified agarose via the attachment of a polyammonium lipophilic adjunct
45
SYNTHESIS AND INVESTIGATION OF ANTIMICROBIAL ALGINATES. Renee
Carrington, Tatiana Hatchett, Teshell Greene, Nadia Hussain, JaimeLee Cohen, Department
of Chemistry and Physical Sciences, PACE University, New York, NY 10038
Alginates are making phenomenal changes in wound management. The texture and properties of this type
of hydrogel has made it easy to devise different methods for its use in wound care. Its absorbency and
firmness has made it a target as a useful surface not only to absorb moisture but also to be used in the
synthesis of antimicrobial surface. Our work involves the modification of these materials by the covalent
attachment of various polyammonium substituents (Figure 1).
O
+
O
N
+
N
R
O
O
H
O
O
H
n
Figure 1 – Antibacterial Polyammonium Alginate
These modified alginates have demonstrated antibacterial characteristics against Pseudomonas aeruginosa,
Streptococcus aureus, and Escherichia coli. It has been found that the antibacterial activity is dependent on
the length of the hydrocarbon group within the polycationic substituent. The chemistry and the results will
be discussed.
IDENTIFYING POLYMERIC BIOMATERIALS: THE ADSORPTION OF
LYSOZYME ON THE POLY (N-ALKYL ACRYLATES) Jennifer Tucci, Robert
Mentore, School of Theoretical and Applied Sciences, Ramapo College of New Jersey,
Mahwah, NJ, 07430
Acrylic polymers such as the poly (n-alkyl acrylates), are materials widely used in the design of biomedical
implants, such as stents, artificial joints, and intraocular lenses. These medical implants and prosthetic
devices are in constant contact with biological fluids. Over time, proteins found in these fluids accumulate
on the surface of the implants, resulting in repeated percutaneous or surgical procedures to eliminate
possible failure of the implanted device. The amount of protein deposition is a significant factor in
determining the most appropriate polymer to be used for implantation. In this research, the adsorption of
lysozyme, a biological protein, to the surfaces of a series of poly (n-alkyl acrylates) was analyzed. A thin
layer of polymer was used to coat the surface of CaF2 discs, then placed into a solution of flowing
lysozyme. The amount of protein adsorption was determined using FTIR Spectroscopy and other
quantitative methods. Results to date suggest that protein adsorption can not be predicted by the length of
the polymer side chain.
THE INFLUENCE OF MOLECULAR WEIGHT ON MONOLAYER
CHARACTERISTICS OF POLY(METHYL METHACRYLATE).Marylynne Andrews
and Robert Mentore, Ramapo College of New Jersey, School of Theoretical and Applied
Sciences, Mahwah, NJ 07430.
Poly(methyl methacrylate) is a ubiquitous acrylic polymer with several useful properties that enable its use
in various applications ranging from replacement glass panels to biomedical implants and prosthetic
devices. An interesting property of poly(methyl methacrylate) is its surfactant nature that enables the
formation of monomolecular films on the surface of a liquid. Monolayer films can be studied by measuring
the surface tension as the film is compressed and expanded between barriers on a Langmuir trough. In the
present studies, monomolecular films were produced from a series of molecular weight standards and the
surface-pressure versus area isotherms were measured. The results of these studies will be presented
showing whether the film characteristics of the polymers are affected by molecular weights over the range
measured.
46