CHEM*4740 TOPICS IN BIO-ORGANIC CHEMISTRY
Winter Semester, 2007
GENERAL INFORMATION AND COURSE OUTLINE
Instructors:
France-Isabelle Auzanneau
Richard A. Manderville
Adrian L. Schwan
MacN 127
Sci Complex 3243
MacN 336
X53809--course co-ordinator
X53963
X58781
Office Hours: as provided by the individual instructors
Prerequisistes:
Chem*3750 Organic Chemistry II
Chem*2580 Introductory Biochemistry
All of the course instructors will assume a working knowledge of the content of the prerequisites
and other preceding courses. Please review old notes as required.
Text: There is no text for this course. The course instructors will provide references as required.
Web-page for section A: www.chemistry.uoguelph.ca/france-isabelle/Chem474carbohydrate.html
Method of Presentation There are three meetings each week (Mon. Wed. Fri. 12:30-1:20 in
MacKinnon 318).
This course provides students will general and specific aspects of key areas in bio-organic
chemistry. The content is divided into certain areas based on the expertise of the instructors and
each instructor has been assigned four weeks of instruction, with the dates and content as follows.
Unit A Auzanneau: Monday Jan. 8 to Friday Feb. 2, 2007 (11 lectures- 1 test)
Carbohydrate chemistry and molecular modeling
Unit B Manderville: Monday Feb. 6 to Friday Mar. 9, 2007 (11 lectures- 1 test)
Nucleotides/nucleosides, solid state synthesis and drug design
Unit C Schwan: Monday Mar. 12 to Wednesday Apr. 4, 2007 (11 lectures)
Topics in phospholipid chemistry and natural product biosynthesis
Course Grade: The final grade will be calculated as follows:
Item
Assigned Problems
Value
30%
Class tests
30%
Final examination
40%
Comments/Details
from Unit A
from Unit B
from Unit C
from Unit A (Feb. 2/07)
from Unit B (Mar. 9/07)
Cumulative; During exam period
Comprised of the following components
Approx. ¼ from Units A and B
Approx. ½ from Unit C
10%
10%
10%
15%
15%
Specific Course Content
Unit A Carbohydrate chemistry and molecular modeling
1. Monosaccharides: configurations, ring size, conformations, mutarotation and anomeric effects.
(1.5 lectures)
2. Biological relevance of carbohydrates in molecular recognition: blood group determinants,
bacterial polysaccharides. (1.5 lectures)
3. Molecular modeling and molecular recognition of biologically active oligosaccharides: degrees
of freedom, important angles, molecular mechanics, NMR and X-ray crystallography. (2 lectures)
3. Synthetic carbohydrate chemistry: synthetic strategies, common protecting groups and
glycosylation methods. (4 lectures)
4. NMR analysis of carbohydrate building blocks: chemical shifts, coupling constants, 1D, 2D
(real life examples). (2 lectures)
Unit B Nucleotides/nucleosides, solid state synthesis and drug design
Small Molecule/DNA Interactions: How DNA-targeting anticancer drugs modify DNA. Both
covalent and noncovalent modes of DNA binding will be discussed.
DNA Alkylation: Covalent modification of DNA by chemical carcinogens and anticancer agents.
Topic will include synthesis of modified (adducted) DNA bases and use of solid-phase DNA
synthesis to incorporate the modified DNA base into a duplex DNA structure.
Drug Design: The design of anticancer agents that target DNA as a mode of activity. This topic
will include the use of combinatorial chemistry to generate families of DNA-targeting anticancer
agents and the use of solid-phase peptide synthesis to alter the DNA groove specificity by DNA
binding drugs.
Unit C Topics in phospholipid chemistry and natural product biosynthesis
Biosynthesis of Natural Products. general principles, sources of atoms and molecule fragments;
biosynthetic routes to acetogenins, alkaloids, terpenes & fatty acids; isotope labelling methods for
elucidation of biosynthetic routes
Phospholipids structures of fatty acids; various phosphorus head groups; physical characteristics;
synthetic methods; lipases and enzymes in chiral organic synthesis, cellular 2nd messengers; lung
surfactant therapy
ONLY VALID EXCUSES ON MEDICAL OR COMPASSIONATE GROUNDS WILL PREVENT A GRADE OF ZERO
FOR ANY MISSED LAB, ASSIGNMENT OR EXAMINATION (SEE CALENDAR SECT. VIII). STUDENTS MAY BE
ASKED TO PROVIDE CERTIFICATION OF ILLNESS. CPES POLICY PREVENTS CHANGES TO THE
GRADING SCHEME FOR INDIVIDUAL STUDENTS, EXCEPT IN CASE OF ILLNESS. MIDTERM PAPERS MAY
BE RETURNED TO THE INSTRUCTOR FOR CORRECTION OF GRADING ERRORS, ONLY WITHIN ONE WEEK
OF THE RETURN OF THE GRADED PAPERS. NO ADDITIONS MUST BE MADE AFTER RETURN OF THE
PAPER. THE INSTRUCTOR MAY REFUSE TO REGRADE A PAPER, AT HIS DISCRETION. THE USE OF
STORED PROGRAMS OR STORED ALPHANUMERIC INFORMATION ON CALCULATORS, DURING
EXAMINATIONS OR TESTS, IS NOT ALLOWED.