COSMOSIL HILIC Application Notebook contains about 200 chromatograms for the separation of polar compounds using COSMOSIL HILIC column. It also describes how the mobile phase conditions, such as buffer pH and salt concentration inÀuence the
separation in HILIC mode
Contents
Hydrophilic Interaction Chromatography
P2
COSMOSIL HILIC
P3
COSMOSIL 2.5HILIC
P5
COSMOSIL Applications
P8
COSMOSIL Applications on Website
P11
COSMOSIL Chromatogram Index
P12
Reference List
P34
7. INDEX
P36
Hydrophilic Interaction Chromatography
The hydrophilic interaction chromatography is a variation of normal phase chromatography. The elution order is similar to that of
normal phase and the sample elution is in the order of increasing hydrophilicity.
Separation Mode
Hydrophilic interaction
chromatography
Hydrophobic interaction
chromatography
Stationary Phase
Hydrophilic Group (or Silica Gel)
Hydrophobic group (C18 etc.)
Mobile Phase
Organic Solvent (CH3CN etc.) / H2O
Main Interaction
Hydrophilic interaction
Hydrophobic interaction
Target Sample
Hydrophilic compounds
Hydrophilic and hydrophobic compounds
Features
䞉 for separation of Hydrophilic compounds
䞉 Suitable for LC/MS
䞉 for the widest range of compounds
䞉 High separation ability
䞉 A wide range of applications
Comparison with C18
COSMOSIL HILIC can separate glycine and glycylglycine without ion-pair reagent. Although C18 column can separate them with
ion-pair reagents, there are some disadvantages such as longer column equilibration time, time-consuming preparation of mobile phase and earlier column deterioration.
COSMOSIL HILIC
without Ion-pair Reagents
COSMOSIL 5C18-PAQ
without
Column Size
Flow Rate
Temperature
Detection
Sample
Injection Volume
4.6 mm I.D. x 250 mm
1.0 ml/min
30Υ
UV 210 nm
(5.0 mg/ml)
1. Glycine
2. Glycylglycine (0.125 mg/ml)
2.0 μl
with Ion-pair Reagents
Mobile Phase
Acetonitrile : 10 mmol/l CH3COONH4 = 60 : 40
2
Mobile Phase
20 mmol/l Phosphatase Buffer (pH2.5)
Mobile Phase
20 mmol/l Phosphatase Buffer (pH2.5)
- 5 mmol/l Sodium 1-Octanesulfonate (Ion-pair Reagent)
HPLC Column for Hydrophilic Interaction
COSMOSIL HILIC
・Triazole bonded stationary phase
・Enhanced hydrophilic interaction
・Alternative selectivity to other HILIC columns
N
NH
N
Triazole
Different Interactions
・Separation of Anionic Compounds
Anionic compounds were used to evaluate the anion-exchange capability. The only COSMOSIL HILIC showed strong
selectivity of anionic compounds against competitors' columns
M company
(HILIC column)
COSMOSIL HILIC
T company
(Amide column)
W company
(HILIC column)
Column Size
Mobile Phase
Flow Rate
Temperature
Detection
Sample
Injection Volume
4.6 mm I.D. x 250 mm
Acetonitrile : 10 mmol/l Phosphate Buffer (pH7.0) = 50 : 50
1.0 ml/min
30Υ
UV 210 nm
1. Oxamic Acid (0.4 mg/ml)
2. Oxalic Acid (2.0 mg/ml)
1.0 μl
O
NH2
HO
3
O
O
1. Oxamic Acid
HO
OH
O
2. Oxalic Acid
・Separation of Acidic, Basic and Neutral Compounds
Acidic (Glyceric Acid), basic (Tris) and neutral (meso-Erythritol) compounds were used for evaluation of anion and cationexchange characteristics. The separation factor D(Acid/Neutral) indicates its anion-exchange capability and the factor D(Basic/
Neutral) shows its cation-exchange effect.
COSMOSIL HILIC
M companyHILIC column)
Ș(Basic/Neutral) = 4.45
Ș(Acidic/Neutral) = 1.71
T company (Amide column)
Ș(Basic/Neutral) = 3.07
Ș(Acidic/Neutral) = 2.04
W company (HILIC column)
Ș(Basic/Neutral) = 5.03
Ș(Acidic/Neutral) = 1.47
Ș(Basic/Neutral) = 1.48
Ș(Acidic/Neutral) = 4.36
Column Size
Mobile Phase
Flow Rate
Temperature
Detection
Sample
4.6 mm I.D. x 250 mm
Acetonitrile : 50mmol/l CH3COONH4 = 80 : 20
1.0 ml/min
30Υ
ELSD
1. meso-Erythritol (1.0 mg/ml)
(1.0 mg/ml)
2. Tris
(2.0 mg/ml)
3. Glyceric Acid
3.0 μl
Injection Volume
OH
OH
HOOC
HO
OH
OH
OH
H2N
OH
OH
OH
1. meso-Erythritol
Neutral
2. Tris
Basic
3. Glyceric Acid
ࠉAcidic
3
Different Interactions
・Separation by Hydrophilic Interaction
The retention mechanism of COSMOSIL HILIC is the combination of hydrophilic interaction and anion-exchange capability, and
the retention can be controlled by changing the mobile phase.
Hydrophilic Interaction (Low)
Ionic Interaction
(Low)
Hydrophilic Interaction (Low)
Ionic Interaction
(High)
Hydrophilic Interaction (High)
Ionic Interaction
(Low)
Suppress ionic
interaction by
increasing salt
concentration
Mobile Phase
Acetonitrile : 10 mmol/l CH3COONH4 = 50 : 50
Column Size
Flow Rate
Temperature
Detection
Sample
Injection Volume
Enhance hydrophilic interaction
by increasing organic solvent concentration.
Mobile Phase
Acetonitrile : 100 mmol/l CH3COONH4 = 50 : 50
4.6 mm I.D. x 250 mm
1.0 ml/min
30Υ
UV 245 nm
1. Isoascorbic AcidࠝErythrbic Acidࠞ (0.5 mg/ml)
(0.5 mg/ml)
2. Ascorbic Acid
2.0 μl
Mobile Phase
Acetonitrile : 100 mmol/l CH3COONH4 = 80 : 20
HO
1. Isoascorbic Acid
䚷䚷䛊Erythorbic Acid䛋
HO
H
HO
HO
2. Ascorbic Acid
H
H
O
HO
O
HO
HO
H
OH
O
O
Melamine Analysis
Melamine analysis and LC/MS/MS using COSMOSIL HILIC.
7.5e4
7.0e4
TIC
Melamine(Positive ESI)
6.5e4
6.0e4
5.5e4
5.0e4
4.5e4
4.0e4
3.5e4
3.0e4
2.5e4
2.0e4
1.5e4
1.0e4
1.88
5000.0
0.0
0.5
1.0
1.5
2.0
4.92
2.5
3.0
3.5
4.0
4.5
5.0
5.5
Time,min
6.0
6.5
7.0
7.5
8.0
8.5
9.0
9.5
10.0
Combination with C18 Columns
Column Size
Mobile Phase
3,4,5
Flow Rate
Temperature
Detection
1 2
6
COSMOSIL 5C18-AR-II
7
COSMOSIL HILIC
4.6 mm I.D. x 250 mm
5C18-AR-Ⅱ A:10%Acetonitrile/0.1%TFA = 10/90
B:10%Acetonitrile/0.1%TFA = 30/70
B 0→100％ 20min linear gradient
HILIC
Acetonitrile/10mmol/l Phosphate Buffer(pH7)= 70/30
1.0 ml/min
30Υ
UV 220 nm
Sample
(0.5 μg)
1. Angiotensin II, [Sar1, Thr8]
(0.5 μg)
2. Angiotensin II, [Sar1, Ala8]
1
8
3. Angiotensin II, Des-Asp - [Ile ] (0.5 μg)
(0.5 μg)
4. Angiotensin II, [Asn1, Val5]
(0.5 μg)
5. Angiotensin II, [Sar1, Ile8]
(0.5 μg)
6. Angiotensin II, [Val5]
(0.5 μg)
3
7. Angiotensin II, (Human)
4
Separate peak No.3-6
by COSMOSIL HILIC
0
4
5
10
15
20 (min)
5
6
Ordering Information
Product Name
COSMOSIL HILIC
Packed Column
Column Size
Product Number
1.0 mm I.D. x 150 mm
1.0 mm I.D. x 250 mm
2.0 mm I.D. x 30 mm
2.0 mm I.D. x 50 mm
2.0 mm I.D. x 100 mm
2.0 mm I.D. x 150 mm
2.0 mm I.D. x 250 mm
3.0 mm I.D. x 150 mm
3.0 mm I.D. x 250 mm
07869-11
07870-71
08568-21
07052-91
08569-11
07054-71
07489-91
07871-61
07872-51
4.6 mm I.D. x 150 mm
07056-51
4.6 mm I.D. x 150 mm
3 lots set
09385-23
Product Name
COSMOSIL HILIC
Packed Column
COSMOSIL HILIC
Guard Column
Column Size
Product Number
4.6 mm I.D. x 250 mm
10.0 mm I.D. x 150 mm
10.0 mm I.D. x 250 mm
20.0 mm I.D. x 250 mm
28.0 mm I.D. x 250 mm
4.6 mm I.D. x 10 mm
10.0 mm I.D. x 20 mm
20.0 mm I.D. x 20 mm
20.0 mm I.D. x 50 mm
28.0 mm I.D. x 50 mm
07057-41
05564-51
07059-21
07060-81
07875-21
07055-61
07058-31
07854-91
07873-41
07874-31
Ultra-High Performance Column for HILIC Analysis
COSMOSIL 2.5HILIC
・Ultra-High Performance using 2.5 ȝm particles
Ultra-High-Speed Analysis (Oxidation marker analysis)
COSMOSIL 2.5HILIC can be used with any conventional LC systems.
COSMOSIL Application Data
Column:
Column size:
Mobile phase:
Flow rate:
Temperature:
Detection:
Sample:
Inj. Vol:
HILIC (5䃛m)
2.5HILIC (2.5䃛m)
(4.6mmI.D.-250mm)
(3.0mmI.D.-100mm)
Acetonitrile/ 10mmol/l Ammonium Acetate = 80/20
1.0 ml/min
40°C
UV249nm
Analysis time: 1/6
1; Creatinine
(0.1mg/ml)
2; 2'-Deoxyguanosine
(0.1mg/ml)
3; 8-Hydroxy-2'-Deoxyguanosine (0.1mg/ml)
4; 8-Hydroxy Guanosine
(0.1mg/ml)
1.0μl
NACALAI TESQUE, INC
Ordering Information
Product Name
COSMOSIL 2.5HILIC
Packed Column
Column Size
Product Number
2.0 mm I.D. x 50 mm
2.0 mm I.D. x 75 mm
2.0 mm I.D. x 100 mm
2.0 mm I.D. x 150 mm
11766-21
11768-01
11769-91
11770-51
Product Name
COSMOSIL 2.5HILIC
Packed Column
Column Size
Product Number
3.0 mm I.D. x 50 mm
3.0 mm I.D. x 75 mm
3.0 mm I.D. x 100 mm
3.0 mm I.D. x 150 mm
11771-41
11772-31
11773-21
11774-11
5
Selection guide of mobile phase
COMOSIL HILIC column generates retention and separation by hydrophilic interaction (mainly hydrogen bond) and anion-exchange. Refer to following recommendations to select an appropriate mobile phase condition.
(1) The effect of organic solvent type and content
In general, acetonitrile/water is used as mobile phase.
Retention increases as water content in the mobile phase decreased. (Fig.1)
Use acetonitrile content in the mobile phase within the range of 0-95% (in general 50-95%).
Methanol/water generates shorter retention than acetonitrile/water. (Fig.2)
Use only HPLC grade solvent
8
meso-Erythritol
Tris(hydroxymethyl)
Aminomethane
Guanidoacetic Acid
4
meso-Erythritol
7
Leucine
6
k'
8
Leucine
6
Tris(hydroxymethyl)
Aminomethane
5
k'
•
•
•
•
•
4
3
2
2
1
0
65
70
75
80
85
90
95
100
0
Acetonitorile
Acetonitrile content(%)
Methanol
Fig.1 The effect of acetonitrile content on retention
Fig.2 Difference of acetonitrile and methanol on retention
Column; COSMOSIL HILIC
Mobile phase; Acetonitrile/ 10mmol/l CH3COONH4
Column; COSMOSIL HILIC
Mobile phase; Organic solvent/ 10mmol/l CH3COONH4 = 90/10
(2) The effect of buffer pH
• Keep pH of the mobile phase within the range of 2-7.5.
• The buffer around neutrality generates larger retention. (Fig.3)
4.5
meso-Erythritol
4
Leucine
3.5
Tris(hydroxymethyl)
Aminomethane
Guanidoacetic Acid
k'
3
2.5
2
1.5
1
Fig.3 The effect of buffer pH on retention
0.5
0
2
3
4
5
6
7
8
9
Column; COSMOSIL HILIC
Mobile phase; Acetonitrile / 10mmol/l buffer = 90/10
pH
(3) The effect of salt type and concentration
• When analyze ionic compounds, add salts or buffers in the mobile phase.
• When mobile phase has high acetonitrile content, note dissolubility of the salt. The dissolubility of phosphate buffers used
widely in reversed phase chromatography is low in acetonitrile. Therefore use of phosphate buffers is not recommended.
Keep the concentration of acetonitrile under 70% if use a phosphate buffer. Check that the salt does not precipitate when
mixed with acetonitril before use.
• Ammonium acetate or formic acid ammonium buffers are recommended because they are soluble in high acetonitrile content.
• Use the buffer concentration within the range of 5 - 100mmol/l. Moreover, check that the salt does not precipitate after mixing
buffer and acetonitrile.
• High salt concentration inhibits ion exchange capability and decreases retention. (Fig.4)
• Run mobile phase through membrane ¿lter (less than 0.45ȝm in pore size) before use.
10
Benzoic Acid
8
k'
6
4
2
0
Fig.4 The effect of salt concentration on retention
0
25
50
75
Buffrer Concentration(mmol/l)
6
100
Column; COSMOSIL HILIC
Mobile phase; Acetonitrile / 10mmol/l CH3COONH4 = 50/50
(4) Selection of mobile phase
Following are the recommended mobile phases for different compound types.
→ Acetonitrile / Water = 90/10
→ Acetonitrile / 10mmol/l CH3COONH4 = 90/10
→ Acetonitrile / 10mmol/l CH3COONH4 = 70/30
→ Acetonitrile / 10mmol/l CH3COONH4 = 50/50
Neutral compounds
Basic compounds
Amphoteric compounds
Acidic compounds
↓ not eluted
Acetonitrile / 10mmol/l Phosphate buffer (pH7.0)= 50/50
(5) Two interactions (hydrophilic interaction and anion exchange capability)
The retention mechanism of COSMOSIL HILIC is the combination of hydrophilic interaction and anion-exchange, and the retention can be controlled by changing the mobile phase. More speci¿cally, the hydrophilic interaction can be enhanced by increasing the organic solvent concentration while suppressing the ionic interaction with high salt concentration.
Ionic Interaction (High)
+
HO
Hydrophilic Interaction (High)
+
Hydrophilic Interaction (Low)
Sample:
Ionic Interaction (Low)
HO
H
H
1. Isoascorbic Acid HO
䚷䚷䛊Erythorbic Acid䛋
Enhance hydrophilic interaction
by increasing acetonitrile concentration
O
HO
O
HO
Suppress ionic interaction
2. Ascorbic Acid
by decreasing salt concentration
H
HO
Mobile Phase：
Acetonitrile:10 mmol/l CH3COONH4=50:50
Mobile Phase：
Acetonitrile:100 mmol/l CH3COONH4=80:20
HO
H
OH
O
O
(6) Improvement of peak shape
Try following if peak shape is tailing. The peak shape might improve.
• Add 5mmol/l EDTA to mobile phase.
• Change to citrate buffer. (i. e. 10 mmol/l citrate buffer pH7.0)
80%Acetonitrile/
10mM CH3COONH4
80%Acetonitrile/
10mM CH3COONH4+5mmol/l EDTA
Column
Flow rate
Temperature
Detection
Sample
COSMOSIL HILIC(4.6mmI.D.-250mm)
1.0ml/min
30oC
UV254nm
Tryptophan(1ng)
Fig.5 Improvement of peak shape
(7) Others
• Use scrupulously degassed mobile phase. Air bubbles generate detection noise and accelerate column deterioration.
• We recommend keeping the chromatography conditions constant, since frequent changes of mobile phase shorten column
life.
7
8
9
10
COSMOSIL Applications
COSMOSIL Application has more than 7,000 applications using COSMOSIL columns. Setting optimal HPLC experimental
parameters is the one of the most important processes that requires experience and time. COSMOSIL Application provides
you with sample analysis conditions with widely used ODS columns and other specialty columns.
Visit COSMOSIL top page at
http://www.nacalai.co.jp/global/cosmosil/
Search Result
Click
Applicatio are search by
Applications
1. Sample Category
2. Sample Name
3. CAS No.,
4. Column Name
5. Particle Size
Click
OSMOSIL Applica
COSMOSIL
Application
COSMOSIL Application Data
5C18-MS-II
5PE-MS
NAP
Column:
Column size: 4.6mmI.D.-150mm
Mobile phase: Methanol/ 20mmol/l Phosphate
buffer(pH2.5)
5C18-MS-II = 40/60
5PE-MS
= 60/40
NAP
= 80/20
Flow rate:
1.0 ml/min
Temperature: 30 C
Detection:
UV254nm
Sample:
1; Palmatine (0.2 g)
2; Berberine (0.2 g)
OMe
O
OMe
N+
MeO
OMe
Click
Cl-
O
N+
MeO
OMe
Cl-
NACALAI TESQUE, INC
AP-1024
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
Reference List
References list
No.
Title
Characterization of the decomposition
of compounds derived from
1
imidazolidinyl urea in cosmetics and
patch test materials
A simple graphical representation of
2 selectivity in hydrophilic interaction
liquid chromatography
Comparison of 2-amino-[3-11C]
isobutyric acid and 2-deoxy-23 [18F]Àuoro-D-glucose in nude mice
with xenografted tumors and acute
inÀammation
4
5
6
7
8
9
In Vitro and in Vivo Metabolism of
Verproside in Rats
Functional expression of carnitine/
organic cation transporter OCTN1
in mouse brain neurons: Possible
involvement in neuronal differentiation
Characterization and use of hydrophilic
interaction liquid chromatography type
stationary phases in supercritical Àuid
chromatography
Analysis of 8-hydroxy-2ƍdeoxyguanosine in human urine using
hydrophilic interaction chromatography
with tandem mass spectrometry
A NOVEL NORMAL PHASE
HPLC METHOD FOR THE
QUANTIFICATION OF N-FORMYL
IMPURITY IN AZACITIDINE ACTIVE
PHARMACEUTICAL INGREDIENTS
AND PHARMACEUTICAL DOSAGE
FORMS
Determination of Histamine in
Seafood by Hydrophilic Interaction
Chromatography/Tandem Mass
Spectrometry
Triazole-Linked DNA as a Primer
10 Surrogate in the Synthesis of FirstStrand cDNA
Retention and selectivity of stationary
11 phases for hydrophilic interaction
chromatography
Chromatographic characterization
of hydrophilic interaction liquid
12 chromatography stationary phases:
Hydrophilicity, charge effects, structural
selectivity, and separation ef¿ciency
The different decomposition properties
13 of diazolidinyl urea in cosmetics and
patch test materials
Stationary and mobile phases
14 in hydrophilic interaction
chromatography: a review
Degradation of N-Acetyl-Dglucosamine and D-Glucosamine in
15
Subcritical Water and Properties of the
Degradation Products
Determination of isoascorbic acid in
¿sh tissue by hydrophilic interaction
16
liquid chromatography–ultraviolet
detection
AUTHOR
JOURNAL
ISSUE
PAGE
YEAR
Takahiro Doi, Akihiro Takeda, Akiko
Asada, Keiji Kajimura
Contact Dermatitis
67 (5)
284–292
2012
Mohammed E.A. Ibrahim, Yang Liu,
Charles A. Lucy
Journal of
Chromatography A
1260
126-131
2012
Nuclear Medicine
Communications
33 (10)
1058–
1064
2012
Molecules
17 (10)
1199012002
2012
Neurochemistry
International
In Press
Tsuji, Atsushi B; Kato, Koichi;
Sugyo, Aya; Okada, Maki; Sudo,
Hitomi; Yoshida, Chisato; Wakizaka,
Hidekatsu; Zhang, Ming-Rong; Saga,
Tsuneo
Min Gi Kim, Deok-Kyu Hwang, HyeonUk Jeong, Hye Young Ji, Sei-Ryang
Oh , Yongnam Lee, Ji Seok Yoo, Dae
Hee Shin and Hye Suk Lee
Noritaka Nakamichi, Takayuki
Taguchi, Hiroshi Hosotani, Tomohiko
Wakayama, Takuya Shimizu, Tomoko
Sugiura, Shoichi Iseki, Yukio Kato,
Caroline West, Syame Khater, Eric
Lesellier
Journal of
Chromatography A
1250
182-195
2012
Chiemi Hosozumi, Akira Toriba,
Thanyarat Chuesaard, Takayuki
Kameda, Ning Tang, Kazuichi
Hayakawa
Journal of
Chromatography B
893-894
173-176
2012
35 (8)
10701080
2012
28 (2)
179-182
2012
6 (11)
29562960
2011
T. Satyanarayana Raju, L.
Journal of Liquid
Kalyanaraman, K. S. V. Raghavachary Chromatography &
& P. Yadagiri Swamy
Related Technologies
Tatsuo YOSHIDA, Hirotoshi HAMADA,
Hiroshi MURAKAWA, Hidekazu
Analytical Sciences
YOSHIMOTO, Toshiaki TOBINO, Kei
TODA
Dr. Tomoko Fujino, Dr. Ken-ichi
Yasumoto, Naomi Yamazaki, Ai
Chemistry – An Asian
Hasome, Prof. Kazuhiro Sogawa, Prof. Journal
Hiroyuki Isobe
Yong Guo, Sheetal Gaiki
Journal of
Chromatography A
1218 (35)
59205938
2011
Yuusuke Kawachi, Tohru Ikegami,
Hirotaka Takubo, Yuka Ikegami,
Masatoshi Miyamoto, Nobuo Tanaka
Journal of
Chromatography A
1218 (35)
59035919
2011
Takahiro Doi, Keiji Kajimura, Shuzo
Taguchi
Contact Dermatitis
65 (2)
81-91
2011
Pavel Jandera
Analytica Chimica Acta
692 (1-2)
1-25
2011
Rongchun WANG, Takashi
KOBAYASHI and Shuji ADACHI
Food Science and
Technology Research
17 (4)
273-278
2011
397 (6)
21992210
2010
56 (1)
60-67
2010
Spyros Drivelos, Marilena E. Dasenaki Analytical and
and Nikolaos S. Thomaidis
Bioanalytical Chemistry
Toshiyuki AKACHI, Yasuyuki SHIINA,
Hepatoprotective Effects of Flavonoids
Yayoi OHISHI, Takumi KAWAGUCHI,
from Shekwasha (Citrus depressa)
17
Hirokazu KAWAGISHI, Tatsuya
against D-Galactosamine-Induced
MORITA, Makoto MORI and Kimio
Liver Injury in Rats
SUGIYAMA
34
2012
J. Nutr Sci Vitaminol
Reference List
No.
Title
A Novel Glucosylation Reaction
on Anthocyanins Catalyzed
18 by Acyl-Glucose–Dependent
Glucosyltransferase in the Petals of
Carnation and Delphinium
Molecular identi¿cation of unsaturated
uronate reductase prerequisite for
alginate metabolism in Sphingomonas
sp. A1
Inhibitory Effects of Acylated Acyclic
Sesquiterpene Oligoglycosides from
20 the Pericarps of Sapindus rarak on
Tumor Necrosis Factor-Į-Induced
Cytotoxicity
Approach to hydrophilic interaction
chromatography column selection:
21
Application to neurotransmitters
analysis
Medicinal Flowers. Part 29.
Acylated Oleanane-Type Triterpene
Bisdesmosides: Perennisaponins G,
22
H, I, J, K, L, and M with Pancreatic
Lipase Inhibitory Activity from the
Flowers of Bellis perennis
19
AUTHOR
JOURNAL
Yuki Matsuba, Nobuhiro Sasaki,
Masayuki Tera, Masachika Okamura,
Yutaka Abe, Emi Okamoto, Haruka
Nakamura, Hisakage Funabashi,
The Plant Cell
Makoto Takatsu, Mikako Saito, Hideaki
Matsuoka, Kazuo Nagasawa and
Yoshihiro Ozekia
Ryuichi Takasea, Akihito Ochiai, Bunzo Biochimica et Biophysica
Mikami, Wataru Hashimoto, Kousaku Acta (BBA) - Proteins &
Murata,
Proteomics
Toshio Morikawa, Yuanyuan Xie,
Kiyofumi Ninomiya, Masaki Okamoto,
Chem. Pharm. Bull.
Osamu Muraoka, Dan Yuan, Masayuki
Yoshikawa and Takao Hayakawa
ISSUE
PAGE
YEAR
22 (10)
33743389
2010
1804 (9)
19251936
2010
58 (9)
12761280
2010
1217 (18)
30913104
2010
Raluca-Ioana Chirita, Caroline West,
Adriana-Luminita Finaru, Claire Elfakir
Journal of
Chromatography A
Toshio Morikawa, Xuezheng Li, Eriko
Nishida, Seikou Nakamura, Kiyofumi
Ninomiya, Hisashi Matsuda, Yoshimi
Oda, Osamu Muraoka, Masayuki
Yoshikawa
Helvetica Chimica Acta
93 (3)
573-586
2010
Tetrahedron
66 (2)
504-507
2010
Chem. Pharm. Bull.
57 (2)
198-203
2009
Journal of
Chromatography B
877 (29)
35563562
2009
Journal of
Chromatography B
877 (27)
32153220
2009
Biochemistry
48 (42)
10175–
10182
2009
Phytochemistry
70 (9)
11661172
2009
Biol. Pharm. Bull.
32 (8)
14591461
2009
877 (10)
10051010
2009
Takumi Kawaguchi, Tomohiro Suzuki,
Unusual amino acid derivatives from
Yuka Kobayashi, Shinya Kodani,
23
the mushroom Pleurocybella porrigens Hirofumi Hirai, Kaoru Nagai, Hirokazu
Kawagishi
Structures of Acetylated OleananeYasunobu Asao, Toshio Morikawa,
Type Triterpene Saponins,
Yuanyuan Xie, Masaki Okamoto,
24 Rarasaponins IV, V, and VI, and AntiMakoto Hamao, Hisashi Matsuda,
hyperlipidemic Constituents from the
Osamu Muraoka, Dan Yuan and
Pericarps of Sapindus rarak
Masayuki Yoshikawa
Development and validation of a
reversed-phase high-performance
S. Mutalik, A.K. Hewavitharana, P.N.
25 liquid chromatographic method for
Shaw, Y.G. Anissimov, M.S. Roberts,
quanti¿cation of peptide dendrimers in H.S. Parekh,
human skin permeation experiments
Determination of para-aminohippuric
acid (PAH) in human plasma and urine Phey Yen Han, P. Nicholas Shaw, Carl
26
by liquid chromatography–tandem
M.J. Kirkpatrick
mass spectrometry
Oxidation of Methionine to
Alexander V. Peskin, Rufus Turner,
Dehydromethionine by Reactive
27
Ghassan J. Maghzal, Christine C.
Halogen Species Generated by
Winterbourn and Anthony J. Kettle
Neutrophils
Toshio Morikawa, Yuanyuan Xie,
Yasunobu Asao, Masaki Okamoto,
Oleanane-type triterpene
oligoglycosides with pancreatic lipase Chihiro Yamashita, Osamu
28
inhibitory activity from the pericarps of Muraoka, Hisashi Matsuda, Yutana
Sapindus rarak
Pongpiriyadacha, Dan Yuan, Masayuki
Yoshikawa
Direct Evidence for Ef¿cient
Keisuke Mitsuoka, Ikumi Tamai,
Transport and Minimal Metabolism
Yasushi Morohashi, Yoshiyuki Kubo,
29 of L-Cephalexin by Oligopeptide
Ryoichi Saitoh, Akira Tsuji and Yukio
Transporter 1 in Budded Baculovirus
Kato
Fraction
Simultaneous measurement of
Takahiro Doi, Keiji Kajimura, Satoshi
diazolidinyl urea, urea, and allantoin
30
Takatori, Naoki Fukui, Shuzo Taguchi,
in cosmetic samples by hydrophilic
Shozo Iwagami
interaction chromatography
A Perspective of Hydrophilic Interaction
Chromatography -Development and
Tohru Ikegami, Hirotaka Takubo,
31
the Characteristics of the separation
Nobuo Tanaka
mode
Tetrodotoxin poisoning evidenced by
Hsiao-Chin Jen, Shin-Jung Lin, Yungsolid-phase extraction combining with
32
Hsiang Tsai, Chun-Hsiang Chen, Zuliquid chromatography–tandem mass
Chun Lin, Deng-Fwu Hwang,
spectrometry
Journal of
Chromatography B
Chromatography
29 (2)
Journal of
Chromatography B
871 (1)
2008
95-100
2008
35
INDEX
Sample name
A
Acesulfame
10
12
Creatine
12
Creatinine
Acetrizoic Acid
12
Cyanoacetic Acid
Page
11
17
10, 17
17
Acrylic Acid
12
Cyanuric Acid
L-Į-Alanine
12
L-Cysteine
17
ȕ-Alanine
12
L-(-)-Cystine
18
11
Cytidine
18
11, 12
Cytosine
18
p-Aminobenzamidine
12
p-Aminobenzoic Acid
8, 17
2'-Deoxyguanosine
10
13
3,4-Diaminobenzoic Acid
18
D
4-Amino-n-butyric Acid [GABA]
13
3,5-Diaminobenzoic Acid
18
6-Aminohexanoic Acid [6-Amino-n-caproic Acid]
13
2,4-Diaminophenol
18
5-Aminolevulinic Acid
13
DL-2,6-Diaminopimelic Acid
18
2-Aminopyridine
13
DL-2,3-Diaminopropionic Acid
18
3-Aminopyridine
13
Diatrizoic Acid
19
5-Amino-1H-tetrazole
13
Diethylene Glycol
8
3-Amino-1H-1,2,4-triazole
13
Dipicolinic Acid
19
5-Aminouracil
14
Dithiouracil
19
Ammelide
8
L-DOPA
19
Ammeline
8
Dopamine
19
Amphotericin B
14
Angiotensin I (Human)
14
meso-Erythritol
3, 9, 19
5, 14
Ethylene Glycol
9
Angiotensin II (Human)
1
5
Angiotensin II, [Asn ,Val ]
5, 8, 14
Angiotensin II, [Sar1,Ala8]
5, 14
Angiotensin II, [Sar1,Ile8]
1
8
Angiotensin II, [Sar ,Thr ]
E
L-(+)-Ergothioneine
19
Famotidine
19
Folic Acid
20
5, 8, 14
Folinic Acid
20
5, 14
Formamide
Angiotensin II, [Val5]
5, 8, 15
Angiotensin II, Des-Asp1-[Ile8]
5, 8, 15
L-Arginine
F
D-Fructose-6-phosphate
15
Ascorbic Acid
4, 7, 8
L-(+)-Ascorbic Acid[Vitamin C]
8, 15
20
9, 20
Fuchsine, Acid [Rubin S]
20
Fumaric Acid
20
GABA[4-Amino-n-butyric Acid]
13
Gluconic Acid
20
15
Glucose
9
Aspartame
10
D-Glucose-6-phosphate
9, 20
L-Aspartic Acid
15
Į-D-Glucose-1-phosphate
9, 21
6-Azauracil
15
D-Glucuronic Acid
L-Asparagine
G
21
Aztreonam
15
L-Glutamic Acid
21
Benzamidine
16
L-Glutamine
21
16
Glutaric Acid
21
Glutathione(Reduced Form)
21
3,9
Benzenesulfonic Acid
36
Choline Hydrogen Tartrate
Acetazolamide
Allantoin
C
Sample name
C
Acetamide
Allantoic Acid
B
Page
Benzoic Acid
10, 16
Benzylamine
16
Glyceric Acid
Bromoacetic Acid
16
DL-Glyceric Acid
21
Cacotheline
16
Glycerol
8,9
Caffeine
10
Glycinamide
Camostat
16
Glycine
L-Carnitine
16
Glycolic Acid
22
2, 9, 22
Ceftriaxone
17
Glycylglycine
Chloroacetic Acid
17
Guanidoacetic Acid
Citrazinic Acid
17
L-Citrulline
Choline Chloride
21
2, 9, 22
22
1,2,6-Hexanetriol
22
8
L-Histidine
22
11
L-Homocystine
22
H
INDEX
Sample name
H
I
L-Homoserine
Page
22
Sample name
P
Perennisaponin K
Page
34, 35
Hydantoic Acid
23
L-(-)-Phenylalanine
28
Hydantoin
23
p-Phenylenediamine
28
Hydroxylamine-O-sulfonic Acid
23
L-(+)-Į-Phenylglycine
28
8-Hydroxy-2'-Deoxyguanosine
10
Phosphocreatine
28
8-Hydroxy Guanosine
10
O-Phospho-L-serine
28
cis-4-Hydroxy-D-proline
23
Picolinic Acid
28
L-Hydroxyproline [trans-4-Hydroxy-L-proline]
23
Pivalic Acid
28
N-Hydroxysuccinimide
23
Procaterol
28
23
L-Proline
29
Propionic Acid
29
Indigo carmine
Isoascorbic Acid[Erythorbic Acid]
4, 7, 8
D-Isoascorbic Acid
23
Pyridoxine[Vitamin B6]
Isocinchomeronic Acid [Pyridine-2,5-dicarboxylic Acid]
24
Pyruvic Acid
29
Isoleucine
9
Q
Quinine
10
L-Isoleucine
24
R
Isonicotinic Acid 24
Isonicotinohydrazide
24
S
8, 29
RiboÀavin[Vitamin B2]
8, 32
Ribose-5-phosphate
29
D-Saccharic Acid
29
Isopropyl -ȕ-D-1-thiogalactopyranoside [IPTG]
24
Saccharin
10
K
Kojic Acid
24
Sarcosine
29
L
Leucine
9
Sebacic Acid
29
L-Leucine
24
L-Serine
30
D-Leucyl-L-tyrosine
24
Sinigrin
L-Lysine
25
Sorbic Acid
Melamine
4, 8, 25
M
N
25
Sulbactam
30
Malic Acid
8
Sulfanilic Acid
30
L-(-)-Malic Acid
25
L-(+)-Tartaric Acid
30
T
Malonic Acid
25
Taurine
Mecobalamin
25
L-Theanine
Metanilic Acid
25
Thiamine[Vitamin B1]
32
L-Methionine
25
2-Thiobarbituric Acid
31
10, 30
31
N-Methylglucamine
26
2-Thiouracil
31
N-Methylhydroxylamine
26
L-Threonine
31
2-Methylimidazole
10
Todralazine
31
31
4-Methylimidazole
10
Trichloroacetic Acid
6-Methyl-2-thiouracil
26
Trimethylene Glycol
Mucic Acid
26
Tris(hydroxymethyl)aminomethane
Murexide
26
Tryptophan
7
1,5-Naphthalenedisulfonic Acid
11
L-Tryptophan
31
L-Tyrosine
32
Nicotinamide
8, 26
Nicotinic Acid
8, 26
U
26
9
3, 9, 31
Uracil
10, 32
Urea
10, 32
Uridine
10, 32
Valine
9
28
Norepinephrine [L-Noradrenaline]
26
DL-Norleucine
27
DL-Norvaline
27
L-Valine
L-Ornithine
27
Vitamin B1[Thiamine]
28
Orotic Acid
27
Vitamin B2 [RiboÀavin]
8, 32
Oxalic Acid
3, 9, 27
Vitamin B6[Pyridoxine]
8, 29
Oxamic Acid
3, 9, 27
Vitamin C[L-(+)-Ascorbic Acid]
8, 15
Oxytocin
P
30
Maleic Acid
L-Noradrenaline [Norepinephrine]
O
Succinic Acid
30
8, 10, 30
V
27
D-Pantothenic Acid
8, 27
Perennisaponin J
34, 35
37
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