Carbohydrate chemistry, biology and medical applications /
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作 者：edited by Hari G. Garg, Mary K. Cowman and Charles A. Hales.
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ISBN：9780080548166
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简介
The finding by Emil Fischer that glucose and fructose on treatment with phenylhydrazine gave the identical osazone led him to the elucidation of stereochemistry of carbohydrates. Since then, progress in the field of carbohydrates has been amazing with the unraveling their basic structure, biosynthesis, immunology, functions, and clinical uses, for pure carbohydrates and for protein-linked carbohydrates (glycoproteins and proteoglycans). The chapters in this book present a logical sequence leading from the chemistry and biochemistry of carbohydrates, followed by their role in various pathological conditions, to carbohydrates as potential therapeutic and diagnostic agents. This book offers a detailed panoramic review of the chemistry and biology of carbohydrates for chemists, biologists and health professionals. Each chapter is authored by contributors expert in the particular area of research.
目录
Preface p. xi
Contributors p. xiii
1 The Development of Carbohydrate Chemistry and Biology Derek Horton p. 1
I Early History p. 1
II The Contribution of Emil Fischer p. 2
III Cyclic Forms p. 5
IV Nomenclature of Carbohydrates p. 8
V General Elucidation of Carbohydrate Structure p. 9
VI Monosaccharide Structure p. 10
VII Oligosaccharide Structure p. 11
VIII Polysaccharide Structure p. 12
IX Carbohydrate Antibiotics p. 14
X Structural Methodology p. 15
XI Carbohydrate Biochemistry p. 18
XII Carbohydrate Antigens and Vaccines p. 20
XIII Conclusion p. 21
2 Carbohydrate Structure Determination by Mass Spectrometry Bo Xie and Catherine E. Costello p. 29
I Glycoproteins and Other Glycoconjugates p. 29
II Instrumentation for Mass Spectrometry Applied to Carbohydrate Structural Determinations p. 34
III Glycan Structural Determination by Mass Spectrometry p. 44
IV Summary p. 52
3 Chemical Synthesis of Complex Carbohydrates Zhongwu Guo p. 59
I Introduction p. 59
II Glycosylation Methods in Carbohydrate Synthesis p. 60
III Strategies for Oligosaccharide Assembly p. 65
IV Chemical Synthesis of Glycosylphosphatidylinositols p. 70
V Conclusion p. 75
4 Enzymatic Synthesis of Oligosaccharides and Conversion to Glycolipids Doris M. Su and Hironobu Eguchi and Chengfeng Xia and Jing Song and Wen Yi and Robert L. Woodward and Peng G. Wang p. 85
I Introduction p. 85
II Oligosaccharide Biosynthesis-Associated Enzymes p. 86
III Sugar Nucleotide Regeneration Systems p. 88
IV Enzymatic Oligosaccharide Synthesis Processes p. 94
V Conversion of Oligosaccharides to Glycolipids p. 99
VI Conclusion p. 102
5 Proteoglycans in the Lung Mara S. Ludwig p. 113
I Introduction p. 113
II Proteoglycans and Normal Lung Structure p. 113
III Contribution to Basic Lung Biology p. 115
IV Contribution of Proteoglycans to Normal Lung Mechanics p. 115
V Proteoglycans and Mechanical Strain p. 116
VI Proteoglycans and the Developing Lung p. 118
VII Role of Proteoglycans in Lung Disease p. 119
VIII Conclusion p. 125
6 Proteoglycans of the Intervertebral Disk Peter J. Roughley p. 133
I Introduction p. 133
II Disk Proteoglycans p. 134
III Aggrecan p. 134
IV Versican p. 139
V Link Protein p. 140
VI Hyaluronan p. 141
VII Small Leucine-Rich Repeat Proteoglycans p. 142
VIII Perlecan p. 145
IX Conclusion p. 146
7 Small Leucine-Rich Repeat Proteoglycans of Skin Paul G. Scott p. 155
I Introduction p. 155
II Glycosaminoglycans and Proteoglycans of Skin p. 155
III Small Leucine-Rich Repeat Proteins/Proteoglycans p. 156
IV Decorin: The Major Small Leucine-Rich Repeat Proteoglycan of Skin p. 157
V Biglycan p. 160
VI Lumican and Fibromodulin p. 161
VII Functions of Skin Leucine-Rich Repeat Proteoglycans p. 162
VIII Involvement of Skin Leucine-Rich Repeat Proteoglycans in Skin Pathology p. 167
IX Summary and Conclusions p. 170
8 Functional Glycosaminoglycans in the Eye Masahiro Zako and Masahiko Yoneda p. 181
I Introduction p. 181
II Glycosaminoglycans in Eye Diseases p. 181
III Glycosaminoglycans as Clinical Applications p. 194
IV Conclusion p. 199
9 Biological Function of Glycosaminoglycans Michael Roth and Eleni Papakonstantinou and George Karakiulakis p. 209
I Introduction p. 209
II Biological Function of Glycosaminoglycans p. 210
III Concluding Remarks p. 217
10 Physiological, Pathophysiological and Therapeutic Roles of Heparin/Heparan sulfate Jin Xie and Saravanababu Murugesan and Robert J. Linhardt p. 227
I Introduction p. 227
II Structure of Heparin and Heparan Sulfate p. 228
III Blood Coagulation Processes p. 229
IV Cell Growth and Differentiation p. 231
V Inflammation p. 234
VI Host Defense and Viral Infection Mechanisms p. 236
VII Cell-Cell and Cell-Matrix Interactions p. 238
VIII Lipid Transport and Clearance Metabolism p. 240
IX Potential Therapeutic Roles of Heparin and Heparan Sulfate p. 242
11 Carbohydrates and Cutaneous Wound Healing Andrew Burd and Lin Huang p. 253
I Introduction p. 253
II Carbohydrate Polymers as Wound Dressings p. 254
III Carbohydrate in Wound Healing Modulation p. 259
IV Carbohydrate in Skin Tissue Engineering p. 264
V Conclusions p. 269
12 Carbohydrates in Human Milk and Infant Formulas Gunther Boehm and Bernd Stahl and Jan Knol and Johann Garssen p. 275
I Introduction p. 275
II Prebiotic Factors in Human Milk p. 276
III Oligosaccharides of Nonhuman Milk Origin p. 277
IV Prebiotic Effect of Nonmilk Oligosaccharides p. 279
V Effect of Intestinal Microbiota on the Immune System: Preclinical Studies p. 283
VI Effect of Intestinal Microbiota on the Immune System: Clinical Trials p. 284
VII Conclusion p. 286
13 Role of Cell Surface Carbohydrates in Development and Disease Michiko N. Fukuda and Tomoya O. Akama and Kazuhiro Sugihara p. 293
I Introduction p. 293
II The Role of Cell Surface Carbohydrates in Reproduction and Development p. 293
III The Role of Cell Surface Carbohydrates in Cancer p. 300
IV Perspective p. 302
14 Therapeutic Use of Hyaluronan-Based Products Endre A. Balazs and Philip A. Band p. 311
I Introduction p. 311
II Ophthalmic Viscosurgery p. 311
III Intra-Articular Hyaluronan: Viscosupplementation p. 314
IV Tissue Augmentation p. 318
V Hyaluronan for Antiadhesion, Wound Healing, and Matrix Engineering p. 322
15 Drug Delivery and Medical Applications of Chemically Modified Hyaluronan Luis Z. Avila and Diego A. Gianolio and Paul A. Konowicz and Michael Philbrook and Michael R. Santos and Robert J. Miller p. 333
I Introduction p. 333
II Conjugation of Active Agents to Hyaluronan p. 334
III Conjugation of Peptides and Proteins to Hyaluronan p. 340
IV Drug Formulations Using Hyaluronan p. 342
V Conclusion/Summary p. 347
16 Carbohydrate Microarrays as Essential Tools of Postgenomic Medicine Xichun Zhou and Gregory T. Carroll and Craig Turchi and Denong Wang p. 359
I Introduction p. 359
II Carbohydrate Microarrays as Essential Tools in the Postgenomics Era p. 360
III Progress in Developing Complementary Platforms of Carbohydrate Microarrays p. 365
IV Conclusion Remarks p. 380
17 Carbohydrate Arrays for Basic Science and as Diagnostic Tools Tim Horlacher and Jose L. de Paz and Peter H. Seeberger p. 387
I Introduction p. 387
II Carbohydrate Microarrays p. 388
III Microarrays of Glycosaminoglycan Oligosaccharides for High-Throughput Screening Glycosaminoglycan-Protein Interactions p. 389
IV Carbohydrate Microarrays to Detect Pathogens and Viruses p. 396
V Conclusions p. 399
Index p. 405
Contributors p. xiii
1 The Development of Carbohydrate Chemistry and Biology Derek Horton p. 1
I Early History p. 1
II The Contribution of Emil Fischer p. 2
III Cyclic Forms p. 5
IV Nomenclature of Carbohydrates p. 8
V General Elucidation of Carbohydrate Structure p. 9
VI Monosaccharide Structure p. 10
VII Oligosaccharide Structure p. 11
VIII Polysaccharide Structure p. 12
IX Carbohydrate Antibiotics p. 14
X Structural Methodology p. 15
XI Carbohydrate Biochemistry p. 18
XII Carbohydrate Antigens and Vaccines p. 20
XIII Conclusion p. 21
2 Carbohydrate Structure Determination by Mass Spectrometry Bo Xie and Catherine E. Costello p. 29
I Glycoproteins and Other Glycoconjugates p. 29
II Instrumentation for Mass Spectrometry Applied to Carbohydrate Structural Determinations p. 34
III Glycan Structural Determination by Mass Spectrometry p. 44
IV Summary p. 52
3 Chemical Synthesis of Complex Carbohydrates Zhongwu Guo p. 59
I Introduction p. 59
II Glycosylation Methods in Carbohydrate Synthesis p. 60
III Strategies for Oligosaccharide Assembly p. 65
IV Chemical Synthesis of Glycosylphosphatidylinositols p. 70
V Conclusion p. 75
4 Enzymatic Synthesis of Oligosaccharides and Conversion to Glycolipids Doris M. Su and Hironobu Eguchi and Chengfeng Xia and Jing Song and Wen Yi and Robert L. Woodward and Peng G. Wang p. 85
I Introduction p. 85
II Oligosaccharide Biosynthesis-Associated Enzymes p. 86
III Sugar Nucleotide Regeneration Systems p. 88
IV Enzymatic Oligosaccharide Synthesis Processes p. 94
V Conversion of Oligosaccharides to Glycolipids p. 99
VI Conclusion p. 102
5 Proteoglycans in the Lung Mara S. Ludwig p. 113
I Introduction p. 113
II Proteoglycans and Normal Lung Structure p. 113
III Contribution to Basic Lung Biology p. 115
IV Contribution of Proteoglycans to Normal Lung Mechanics p. 115
V Proteoglycans and Mechanical Strain p. 116
VI Proteoglycans and the Developing Lung p. 118
VII Role of Proteoglycans in Lung Disease p. 119
VIII Conclusion p. 125
6 Proteoglycans of the Intervertebral Disk Peter J. Roughley p. 133
I Introduction p. 133
II Disk Proteoglycans p. 134
III Aggrecan p. 134
IV Versican p. 139
V Link Protein p. 140
VI Hyaluronan p. 141
VII Small Leucine-Rich Repeat Proteoglycans p. 142
VIII Perlecan p. 145
IX Conclusion p. 146
7 Small Leucine-Rich Repeat Proteoglycans of Skin Paul G. Scott p. 155
I Introduction p. 155
II Glycosaminoglycans and Proteoglycans of Skin p. 155
III Small Leucine-Rich Repeat Proteins/Proteoglycans p. 156
IV Decorin: The Major Small Leucine-Rich Repeat Proteoglycan of Skin p. 157
V Biglycan p. 160
VI Lumican and Fibromodulin p. 161
VII Functions of Skin Leucine-Rich Repeat Proteoglycans p. 162
VIII Involvement of Skin Leucine-Rich Repeat Proteoglycans in Skin Pathology p. 167
IX Summary and Conclusions p. 170
8 Functional Glycosaminoglycans in the Eye Masahiro Zako and Masahiko Yoneda p. 181
I Introduction p. 181
II Glycosaminoglycans in Eye Diseases p. 181
III Glycosaminoglycans as Clinical Applications p. 194
IV Conclusion p. 199
9 Biological Function of Glycosaminoglycans Michael Roth and Eleni Papakonstantinou and George Karakiulakis p. 209
I Introduction p. 209
II Biological Function of Glycosaminoglycans p. 210
III Concluding Remarks p. 217
10 Physiological, Pathophysiological and Therapeutic Roles of Heparin/Heparan sulfate Jin Xie and Saravanababu Murugesan and Robert J. Linhardt p. 227
I Introduction p. 227
II Structure of Heparin and Heparan Sulfate p. 228
III Blood Coagulation Processes p. 229
IV Cell Growth and Differentiation p. 231
V Inflammation p. 234
VI Host Defense and Viral Infection Mechanisms p. 236
VII Cell-Cell and Cell-Matrix Interactions p. 238
VIII Lipid Transport and Clearance Metabolism p. 240
IX Potential Therapeutic Roles of Heparin and Heparan Sulfate p. 242
11 Carbohydrates and Cutaneous Wound Healing Andrew Burd and Lin Huang p. 253
I Introduction p. 253
II Carbohydrate Polymers as Wound Dressings p. 254
III Carbohydrate in Wound Healing Modulation p. 259
IV Carbohydrate in Skin Tissue Engineering p. 264
V Conclusions p. 269
12 Carbohydrates in Human Milk and Infant Formulas Gunther Boehm and Bernd Stahl and Jan Knol and Johann Garssen p. 275
I Introduction p. 275
II Prebiotic Factors in Human Milk p. 276
III Oligosaccharides of Nonhuman Milk Origin p. 277
IV Prebiotic Effect of Nonmilk Oligosaccharides p. 279
V Effect of Intestinal Microbiota on the Immune System: Preclinical Studies p. 283
VI Effect of Intestinal Microbiota on the Immune System: Clinical Trials p. 284
VII Conclusion p. 286
13 Role of Cell Surface Carbohydrates in Development and Disease Michiko N. Fukuda and Tomoya O. Akama and Kazuhiro Sugihara p. 293
I Introduction p. 293
II The Role of Cell Surface Carbohydrates in Reproduction and Development p. 293
III The Role of Cell Surface Carbohydrates in Cancer p. 300
IV Perspective p. 302
14 Therapeutic Use of Hyaluronan-Based Products Endre A. Balazs and Philip A. Band p. 311
I Introduction p. 311
II Ophthalmic Viscosurgery p. 311
III Intra-Articular Hyaluronan: Viscosupplementation p. 314
IV Tissue Augmentation p. 318
V Hyaluronan for Antiadhesion, Wound Healing, and Matrix Engineering p. 322
15 Drug Delivery and Medical Applications of Chemically Modified Hyaluronan Luis Z. Avila and Diego A. Gianolio and Paul A. Konowicz and Michael Philbrook and Michael R. Santos and Robert J. Miller p. 333
I Introduction p. 333
II Conjugation of Active Agents to Hyaluronan p. 334
III Conjugation of Peptides and Proteins to Hyaluronan p. 340
IV Drug Formulations Using Hyaluronan p. 342
V Conclusion/Summary p. 347
16 Carbohydrate Microarrays as Essential Tools of Postgenomic Medicine Xichun Zhou and Gregory T. Carroll and Craig Turchi and Denong Wang p. 359
I Introduction p. 359
II Carbohydrate Microarrays as Essential Tools in the Postgenomics Era p. 360
III Progress in Developing Complementary Platforms of Carbohydrate Microarrays p. 365
IV Conclusion Remarks p. 380
17 Carbohydrate Arrays for Basic Science and as Diagnostic Tools Tim Horlacher and Jose L. de Paz and Peter H. Seeberger p. 387
I Introduction p. 387
II Carbohydrate Microarrays p. 388
III Microarrays of Glycosaminoglycan Oligosaccharides for High-Throughput Screening Glycosaminoglycan-Protein Interactions p. 389
IV Carbohydrate Microarrays to Detect Pathogens and Viruses p. 396
V Conclusions p. 399
Index p. 405
Carbohydrate chemistry, biology and medical applications /
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