http://www.book4doc.com/72910
http://www.book4doc.com/54413
Edited by
Toshimasa Toyo'oka
School of Pharmaceutical Sciences, University of Shizuoka, Japan
ISBN 0-471-98364-0 (alk. paper)
NUMBER OF PAGE:588
List of Contributors xi
Preface xiii
1. Pre-treatment for Real Sample Analysis and Choice of Suitable Reagent 1
Akihiko Nakagawa, and Yukinori Kawahara
1.1. Derivatization for Drugs 1
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
HPLC with Laser-induced Fluorescence Detection after
Immobilized Antibody Extraction
2
1.1.2.2. Enantiospecific Determination of Ibuprofen in Rat
Plasma Using Chiral Fluorescence Derivatization Reagent, (-)-2-
[4-(1-aminoethyl)phenyl]6-methoxybenzoxazole
4
1.1.2.4. Specific Fluorogenic Derivatization of Ivermectin Using
Non-fluorescent Reagents
6
1.1.2.4. Other Methods 8
1.1.3. Conclusion 10
References
Hiroyuki Nakazawa and Koichi Saito
1.2. Derivatization for Agrochemicals 13
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
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
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
1.3. Derivatization for Environmental Contaminants 51
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
Kiyoshi Zaitsu, Masaaki Kai and Kenji Hamase
2. Reagent for UV-VIS Detection 63
2.1. Introduction 64
2.2. Label of Amines and Amino Acids (-NH2, NH) 65
2.2.1. Nitrobenzenes 65
2.2.1.1. 1-Fluoro-2,4-dinitrobenzene (FDNB, 2,4-dinitro-1-
fluorobenzene, Sanger Reagent)
65
2.2.1.2. 4-Fluoro-3-nitrotrifluoromethylbenzene (4-fluoro-3-
nitrobenzotrifluoride) (FNBT)
66
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
(FDAA, 1-Fluoro-2,4-dinitrophenyl-5-L-alanine amide,
Marfey's Reagent)
67
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
(DABITC)
70
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
(DABS-C1, Dabsyl-Cl)
73
2.2.6. 9-Fluorenylmethyl Chloroformate (9-
Fluorenylmethoxycarbonyl Chloride, FMOC-CL, Fluorescence and
UV Detection)
73
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
Moiety
76
2.2.11.1. Polymeric 3,5-Dinitrobenzoyl Tagged Derivatization
Reagent
77
2.2.11.2. Polymeric 6-Aminoquinoline (6-AQ) Tagged
78
Derivatization Reagent
2.2.11.3. Polymeric Benzotriazole Activated Reagent
Containing FMOC Group
78
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
2.7.2. Diethyldithiocarbamate (DDTC) 94
2.7.3. 9-Methylamino-methylanthracene (MAMA) 95
References 95
Masatoshi Yamaguchi, and Junichi Ishida
3. Reagent for FL Detection 99
Abbreviations 100
3.1. Introduction 102
3.2. Reagents for Amines and Amino Acids 103
3.2.1. General Amino Compounds 103
3.2.1.1. Primary Amines and Amino Acids 103
3.2.1.2. Primary and Secondary Amines and Amino Acids 106
3.2.2. Particular Amines and Amino Acids 116
3.2.2.1. Catecholamines 116
3.2.2.2. Tryptophan and Indolamines 117
3.2.2.3. 5-hydroxyindoleamines (Serotonin Related
Compounds)
117
3.2.2.4. Guanidino Compounds 119
3.2.3. Peptides 121
3.2.3.1. General Peptides 121
3.2.3.2. Arginine-containing Peptides 121
3.2.4. Fluorescence Derivatization for CE 121
3.3. Reagents for Organic Acids 121
3.3.1. Carboxylic Acids 121
3.3.1.1. Fatty Acids 129
3.3.1.2. Prostaglandins 130
3.3.1.3. Steroids 131
3.3.1.4. Glucuronic Acid Conjugates 132
3.3.2. α-Keto Acids 133
3.3.3. Sialic Acids and Dehydroascorbic Acid 133
3.4. Reagents for Alcohols 135
3.5. Reagents for Phenols 139
3.6. Reagents for Thiols 141
3.7. Reagents for Aldehydes and Ketones 146
3.8. Reagents for Carbohydrates 150
3.9. Reagents for Dienes 152
3.10. Reagents for Nucleic Acid Related Compounds 153
References 158
Naotaka Kuroda and Kenichiro Nakashima
4. Reagent for CL Detection 167
4.1. Introduction 167
4.2. Label of Amines (-NH2, -NH) 171
4.3. Label of Carboxyl (-COOH) 176
4.4. Label of Hydroxyl (-OH) and Thiol (-SH) 178
4.5. Label of Other Functional Groups 179
4.6. Application 183
References 183
Kenji Shimada, Tomokazu Matsue and Kazutake Shimada
5. Reagents for Electrochemical Detection 191
5.1. Introduction 192
5.1.1. Amperometric Analysis in Flowing Streams 192
5.1.2. Electrochemical Detectors 192
5.1.3. Electrode Material 193
5.1.4. Electrode Configuration 194
5.1.5. Mobile Phase 195
5.1.6. Chemical Derivatization 196
5.2. Labeling of Primary and Secondary Amines 198
5.2.1. o-phthalaldehyde 198
5.2.2. Naphthalene-2,3-dicarbaldehyde 199
5.2.3. Ferrocene 200
5.2.4. Isocyanate and Isothiocyanate 202
5.2.5. Salicylic Acid Chloride 203
5.2.6. 2,4-Dinitrofluorobenzene 204
5.2.7. 1,2-Diphenylethylenediamine 204
5.2.8. Bolton and Hunter Type Reagent 204
5.2.9. Others 205
5.3. Labeling of Carboxy Groups 205
5.4. Labeling of Hydroxy Groups 207
5.5. Labeling of Thiol Groups 208
5.6. Labeling of Other Functional Groups 208
5.7. Applications 211
References 213
6. Derivatization for Resolution of Chiral Compounds 217
6.1. Introduction 218
6.1.1. Fundamentals of Stereochemistry 218
6.1.2. Chirality and Biological Activity 220
6.1.3. Chirality Application as Single Isomers 222
6.2. Resolution of Racemates 223
6.2.1. Direct Resolution 223
6.2.2. Indirect Resolution 223
6.3. Reactions of Various Functional Groups 225
6.3.1. Amines 225
6.3.2. Carboxyls 226
6.3.3. Hydroxyls 227
6.3.4. Thiols and Others 227
6.4. Derivatization for LC Analysis 228
6.4.1. Label for Alcohols 228
6.4.2. Label for Carboxylic Acids 230
6.4.3. Label for Aldehydes and Ketones 231
6.4.4. Label for Other Functional Groups 233
6.5. Derivatization for LC Analysis 233
6.5.1. Label for UV-VIS Detection 235
6.5.1.1. Label for Primary and Secondary Amines 235
6.5.1.2. Label for Carboxylic Acids 240
6.5.1.3. Label for Alcohols 241
6.5.1.4. Label for Other Functional Groups 241
6.5.2. Label for Fluorescence (FL), Laser-Induced Fluorescence
(LIF) and Chemiluminescence (CL) Detection
243
6.5.2.1. Label for Primary and Secondary Amines Including
Amino Acids 249
249
6.5.2.2. Label for Carboxylic Acids 257
6.5.2.3. Label for Alcohols 262
6.5.2.4. Label for Aldehydes and Ketones 266
6.5.2.5. Label for Thiols 266
6.5.2.6. Label for Other Functional Groups 267
6.5.3. Derivatization for Electrochemical (EC) Detection 267
6.6. Derivatization for Capillary Electrophoresis (CE) Analysis 267
6.7. Conclusion and Further Perspective 284
References 284
Index 291
http://www.book4doc.com/54413
Edited by
Toshimasa Toyo'oka
School of Pharmaceutical Sciences, University of Shizuoka, Japan
ISBN 0-471-98364-0 (alk. paper)
NUMBER OF PAGE:588
List of Contributors xi
Preface xiii
1. Pre-treatment for Real Sample Analysis and Choice of Suitable Reagent 1
Akihiko Nakagawa, and Yukinori Kawahara
1.1. Derivatization for Drugs 1
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
HPLC with Laser-induced Fluorescence Detection after
Immobilized Antibody Extraction
2
1.1.2.2. Enantiospecific Determination of Ibuprofen in Rat
Plasma Using Chiral Fluorescence Derivatization Reagent, (-)-2-
[4-(1-aminoethyl)phenyl]6-methoxybenzoxazole
4
1.1.2.4. Specific Fluorogenic Derivatization of Ivermectin Using
Non-fluorescent Reagents
6
1.1.2.4. Other Methods 8
1.1.3. Conclusion 10
References
Hiroyuki Nakazawa and Koichi Saito
1.2. Derivatization for Agrochemicals 13
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
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
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
1.3. Derivatization for Environmental Contaminants 51
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
Kiyoshi Zaitsu, Masaaki Kai and Kenji Hamase
2. Reagent for UV-VIS Detection 63
2.1. Introduction 64
2.2. Label of Amines and Amino Acids (-NH2, NH) 65
2.2.1. Nitrobenzenes 65
2.2.1.1. 1-Fluoro-2,4-dinitrobenzene (FDNB, 2,4-dinitro-1-
fluorobenzene, Sanger Reagent)
65
2.2.1.2. 4-Fluoro-3-nitrotrifluoromethylbenzene (4-fluoro-3-
nitrobenzotrifluoride) (FNBT)
66
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
(FDAA, 1-Fluoro-2,4-dinitrophenyl-5-L-alanine amide,
Marfey's Reagent)
67
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
(DABITC)
70
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
(DABS-C1, Dabsyl-Cl)
73
2.2.6. 9-Fluorenylmethyl Chloroformate (9-
Fluorenylmethoxycarbonyl Chloride, FMOC-CL, Fluorescence and
UV Detection)
73
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
Moiety
76
2.2.11.1. Polymeric 3,5-Dinitrobenzoyl Tagged Derivatization
Reagent
77
2.2.11.2. Polymeric 6-Aminoquinoline (6-AQ) Tagged
78
Derivatization Reagent
2.2.11.3. Polymeric Benzotriazole Activated Reagent
Containing FMOC Group
78
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
2.7.2. Diethyldithiocarbamate (DDTC) 94
2.7.3. 9-Methylamino-methylanthracene (MAMA) 95
References 95
Masatoshi Yamaguchi, and Junichi Ishida
3. Reagent for FL Detection 99
Abbreviations 100
3.1. Introduction 102
3.2. Reagents for Amines and Amino Acids 103
3.2.1. General Amino Compounds 103
3.2.1.1. Primary Amines and Amino Acids 103
3.2.1.2. Primary and Secondary Amines and Amino Acids 106
3.2.2. Particular Amines and Amino Acids 116
3.2.2.1. Catecholamines 116
3.2.2.2. Tryptophan and Indolamines 117
3.2.2.3. 5-hydroxyindoleamines (Serotonin Related
Compounds)
117
3.2.2.4. Guanidino Compounds 119
3.2.3. Peptides 121
3.2.3.1. General Peptides 121
3.2.3.2. Arginine-containing Peptides 121
3.2.4. Fluorescence Derivatization for CE 121
3.3. Reagents for Organic Acids 121
3.3.1. Carboxylic Acids 121
3.3.1.1. Fatty Acids 129
3.3.1.2. Prostaglandins 130
3.3.1.3. Steroids 131
3.3.1.4. Glucuronic Acid Conjugates 132
3.3.2. α-Keto Acids 133
3.3.3. Sialic Acids and Dehydroascorbic Acid 133
3.4. Reagents for Alcohols 135
3.5. Reagents for Phenols 139
3.6. Reagents for Thiols 141
3.7. Reagents for Aldehydes and Ketones 146
3.8. Reagents for Carbohydrates 150
3.9. Reagents for Dienes 152
3.10. Reagents for Nucleic Acid Related Compounds 153
References 158
Naotaka Kuroda and Kenichiro Nakashima
4. Reagent for CL Detection 167
4.1. Introduction 167
4.2. Label of Amines (-NH2, -NH) 171
4.3. Label of Carboxyl (-COOH) 176
4.4. Label of Hydroxyl (-OH) and Thiol (-SH) 178
4.5. Label of Other Functional Groups 179
4.6. Application 183
References 183
Kenji Shimada, Tomokazu Matsue and Kazutake Shimada
5. Reagents for Electrochemical Detection 191
5.1. Introduction 192
5.1.1. Amperometric Analysis in Flowing Streams 192
5.1.2. Electrochemical Detectors 192
5.1.3. Electrode Material 193
5.1.4. Electrode Configuration 194
5.1.5. Mobile Phase 195
5.1.6. Chemical Derivatization 196
5.2. Labeling of Primary and Secondary Amines 198
5.2.1. o-phthalaldehyde 198
5.2.2. Naphthalene-2,3-dicarbaldehyde 199
5.2.3. Ferrocene 200
5.2.4. Isocyanate and Isothiocyanate 202
5.2.5. Salicylic Acid Chloride 203
5.2.6. 2,4-Dinitrofluorobenzene 204
5.2.7. 1,2-Diphenylethylenediamine 204
5.2.8. Bolton and Hunter Type Reagent 204
5.2.9. Others 205
5.3. Labeling of Carboxy Groups 205
5.4. Labeling of Hydroxy Groups 207
5.5. Labeling of Thiol Groups 208
5.6. Labeling of Other Functional Groups 208
5.7. Applications 211
References 213
6. Derivatization for Resolution of Chiral Compounds 217
6.1. Introduction 218
6.1.1. Fundamentals of Stereochemistry 218
6.1.2. Chirality and Biological Activity 220
6.1.3. Chirality Application as Single Isomers 222
6.2. Resolution of Racemates 223
6.2.1. Direct Resolution 223
6.2.2. Indirect Resolution 223
6.3. Reactions of Various Functional Groups 225
6.3.1. Amines 225
6.3.2. Carboxyls 226
6.3.3. Hydroxyls 227
6.3.4. Thiols and Others 227
6.4. Derivatization for LC Analysis 228
6.4.1. Label for Alcohols 228
6.4.2. Label for Carboxylic Acids 230
6.4.3. Label for Aldehydes and Ketones 231
6.4.4. Label for Other Functional Groups 233
6.5. Derivatization for LC Analysis 233
6.5.1. Label for UV-VIS Detection 235
6.5.1.1. Label for Primary and Secondary Amines 235
6.5.1.2. Label for Carboxylic Acids 240
6.5.1.3. Label for Alcohols 241
6.5.1.4. Label for Other Functional Groups 241
6.5.2. Label for Fluorescence (FL), Laser-Induced Fluorescence
(LIF) and Chemiluminescence (CL) Detection
243
6.5.2.1. Label for Primary and Secondary Amines Including
Amino Acids 249
249
6.5.2.2. Label for Carboxylic Acids 257
6.5.2.3. Label for Alcohols 262
6.5.2.4. Label for Aldehydes and Ketones 266
6.5.2.5. Label for Thiols 266
6.5.2.6. Label for Other Functional Groups 267
6.5.3. Derivatization for Electrochemical (EC) Detection 267
6.6. Derivatization for Capillary Electrophoresis (CE) Analysis 267
6.7. Conclusion and Further Perspective 284
References 284
Index 291
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