Modern Derivatization Methods for Separation Sciences

588 Pages·1999·6.296 MB·English

by  Toshimasa Toyo'oka

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Modern Derivatization Methods for Separation Sciences
Edited by
Toshimasa Toyo'oka
School of Pharmaceutical Sciences, University of Shizuoka, Japan

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Library of Congress Cataloging-in-Publication Data
Modern derivatization methods for separation sciences/edited by Toshimasa Toyo'oka.
p. cm.
Includes bibliographical references and index.
ISBN 0-471-98364-0 (alk. paper)
1. Chromatographic analysis-Methodology. 2. Derivatization.
I. Toyo'oka, Toshimasa.
QD79.C4M63 1999 98-27197
543'.089-dc21 CIP
British Library Cataloging in Publication Data
A catalogue record for this book is available from the British Library
ISBN 0 471 98364 0
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Typeset in 10/12pt Times by Laser Words, Madras, India
Printed and bound in Great Britain by Bookcraft (Bath) Ltd
This book is printed on acid-free paper responsibly manufactured from sustainable forestry, in which at
least two trees are planted for each one used for paper production

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Contents
List of Contributors xi
Preface xiii
1. Pre-treatment for Real Sample Analysis and Choice of Suitable Reagent 1
1.1. Derivatization for Drugs 1
Akihiko Nakagawa, and Yukinori Kawahara
1.1.1. Introduction 2
1.1.2. Application of Derivatization of Drugs 2
1.1.2.1. Determination of Pravastatin Sodium in Plasma by 2
HPLC with Laser-induced Fluorescence Detection after
Immobilized Antibody Extraction
1.1.2.2. Enantiospecific Determination of Ibuprofen in Rat 4
Plasma Using Chiral Fluorescence Derivatization Reagent, (-)-2-
[4-(1-aminoethyl)phenyl]6-methoxybenzoxazole
1.1.2.4. Specific Fluorogenic Derivatization of Ivermectin Using 6
Non-fluorescent Reagents
1.1.2.4. Other Methods 8
1.1.3. Conclusion 10
References
1.2. Derivatization for Agrochemicals 13
Hiroyuki Nakazawa and Koichi Saito
1.2.1. Introduction 13
1.2.1.1. Sample Preparation 14
1.2.1.2. Derivatization in Food Analysis 15
1.2.2. Analysis of Nutrients 16
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1.2.2.1. Carbohydrates 16
1.2.2.2. Amino Acids and Peptides 17
1.2.2.3. Fatty Acids 22
1.2.2.4. Organic Acids 23
1.2.2.5. Vitamins 24
1.2.2.6. Minerals 26

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1.2.3. Analysis of Food Additives 27
1.2.3.1. Preservatives 27
1.2.3.2. Antioxidants 27
1.2.3.3. Sweeteners 28
1.2.3.4. Emulsifiers 28
1.2.3.5. Other Food Additives 29
1.2.4. Analysis of Veterinary Medicine 29
1.2.4.1. Sulfonamides 30
1.2.4.2. Antibiotics 30
1.2.4.3. Antiparasitic Agents 32
1.2.5. Analysis of Pesticides 34
1.2.6. Analysis of Natural Toxins 35
1.2.6.1. Mycotoxins 35
1.2.6.2. Marine Toxins 39
1.2.6.3. Plant Toxin 42
1.2.7. Analysis of Food Contaminants 42
1.2.7.1. Amines 42
1.2.7.2. Organotin 43
1.2.7.3. Hydroperoxides 45
1.2.7.4. Isocyanate Monomers 45
References 45
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1.3. Derivatization for Environmental Contaminants 51
Kazuo Iwaki
1.3.1. Introduction 51
1.3.2. Environmental Samples 51
1.3.2.1. Gas Sample 51
1.3.2.2. Soil and Various Water Samples 53
1.3.3. Application 55
1.3.3.1. Aldehydes and Ketones in Air 55
1.3.3.2. Aliphatic Amines in Air 57
1.3.3.3. Residual Pesticides and Herbicides in Soil and Water 59
References 62
2. Reagent for UV-VIS Detection 63
Kiyoshi Zaitsu, Masaaki Kai and Kenji Hamase
2.1. Introduction 64
2.2. Label of Amines and Amino Acids (-NH , NH) 65
2
2.2.1. Nitrobenzenes 65
2.2.1.1. 1-Fluoro-2,4-dinitrobenzene (FDNB, 2,4-dinitro-1- 65
fluorobenzene, Sanger Reagent)
2.2.1.2. 4-Fluoro-3-nitrotrifluoromethylbenzene (4-fluoro-3- 66
nitrobenzotrifluoride) (FNBT)
2.2.1.3. 2,4,6-Trinitrobenzene-1-sulfonic Acid (TNBS) 67
2.2.1.4. Na-(2,4-Dinitro-5-fluorophenyl)-L-alanine amide 67
(FDAA, 1-Fluoro-2,4-dinitrophenyl-5-L-alanine amide,
Marfey's Reagent)

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2.2.2. Acetic Anhydride 67
2.2.3. Isocyanates and Isothiocyanates 67
2.2.3.1. Isocyanates 67
2.2.3.2. Phenyl Isothiocyanate (PITC, Edman Reagent) 68
2.2.3.3. Butylisothiocyanate (BITC) 70
2.2.3.4. 4-N,N-Dimethylaminoazobenzene-4'-isothiocyanate 70
(DABITC)
2.2.4. 1,2-Naphthoquinone-4-sulfonate (NQS) 70
2.2.5. Acyl Chlorides 71
2.2.5.1. Benzoyl Chloride 71
2.2.5.2. Dansyl Chloride (DNS-C1) 72
2.2.5.3. 4-N,N-Dimethylaminoazobenzene-4'-sulfonyl Chloride 73
(DABS-C1, Dabsyl-Cl)
2.2.6. 9-Fluorenylmethyl Chloroformate (9- 73
Fluorenylmethoxycarbonyl Chloride, FMOC-CL, Fluorescence and
UV Detection)
2.2.7. Ninhydrin 74
2.2.8. Diethylethoxymethylenemalonate (DEMM) 75
2.2.9. 6-aminoquuinolyl-N-hydroxyuccinimidyl Carbamate (AQC) 76
2.2.10. Disuccinimido Carbonate (DSC) 76
2.2.11. Solid-phase Reagent with UV or VIS Light Absorbing 76
Moiety
2.2.11.1. Polymeric 3,5-Dinitrobenzoyl Tagged Derivatization 77
Reagent
78
2.2.11.2. Polymeric 6-Aminoquinoline (6-AQ) Tagged
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Derivatization Reagent
2.2.11.3. Polymeric Benzotriazole Activated Reagent 78
Containing FMOC Group
2.3. Label of Carboxyl (-COOH) 78
2.3.1. Alkyl Halides 78
2.3.2. Aromatic Amines 79
2.3.3. Hydrazines 81
2.3.4. Hydroxylamine 82
2.4. Label of Hydroxyl (-OH) 84
2.4.1. Acyl Halides 84
2.4.2. Acid Anhydrides 86
2.4.3. Isocyanates 87
2.4.4. Other Reagents 88
2.5. Label of Reducing Carbohydrate 89
2.5.1. Reductive Amination 89
2.5.2. l-Phenyl-3-methyl-5-pyrazolone 91
2.5.3. Post-column Derivatizing Reagent 92
2.6. Label of Thiol (-SH) 92
2.6.1. 2-Halopyridinium Salt 92
2.6.2. Disulfide Reagent 93
2.6.3. Other Reagents 94
2.7. Labelling of Other Compounds 94
2.7.1. l-(2-Pyridyl)-piperazine (PYP) 94
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