Essentials of Carbohydrate Chemistry and Biochemistry 4th edition [Pehme köide]

Preface of the Fourth Edition ix
Preface of the Third Edition xi
Preface of the Second Edition xiii

1 Structure of Saccharides 1
1.1 Structure of Monosaccharides 1
1.2 Structure of Oligosaccharides 24
1.3 Structure of Polysaccharides 30
1.4 Nomenclature of Saccharides 34

2 Protecting Groups for Carbohydrates 45
2.1 Acyl Protecting Groups 47
2.2 Ether Protecting Groups 57
2.3 Selective Protection of the Primary Hydroxyl Group 62
2.4 Cyclic Protecting Groups 65
2.5 Orthoesters as Protecting Groups 81
2.6 Protection of the Anomeric Centre 83
2.7 One-CatalystOne-pot Protections of Per-silylated Sugars 87
2.8 N-Protection for Amino Sugars 89
2.9 Enzymes in Protecting Group Chemistry 93
2.10 Strategic Protecting-Group Sequences on Carbohydrate Scaffolds 94

3 O-Glycoside Synthesis 109
3.1 1,2-trans and 1,2-cis Glycosidation 114
3.2 Factors that Influence a Glycosylation Reaction 117
3.3 The KoenigsKnorr Method 119
3.4 Glycosyl Acetimidates 125
3.5 Thioglycosides 131
3.6 n-Pentenyl Glycosides 136
3.7 Gold-Catalysed Glycoside Synthesis 140
3.8 Synthesis of 2-Deoxy Glycosides 143
3.9 Synthesis of -D-Glucosides and -D-Mannosides 147
3.10 Synthesis of 2-Acetamido-2-Deoxy Glycosides 154
3.11 Solid-Phase Oligosaccharide Synthesis 161
3.12 Glycoside Synthesis Employing Enzymes 163
3.13 Glycosylation Strategies 170

4 Important Modifications of the Sugar Ring 187
4.1 ActivationSubstitution Reactions at the Carbohydrate Ring: Deoxyhalo
Derivatives 187
4.2 Deoxygenation of Carbohydrates 198
4.3 Epimerisations 202
4.4 From Azido to Amino and More: N-Functionalised Sugars 205
4.5 Important Unsaturated Saccharides 208
4.6 Unexpected Journeys of Sugars 219

5 Structure and Biosynthesis of Glycoconjugates 233
5.1 Size, Diversity and Representation 233
5.2 Structures of Glycoconjugates 236
5.3 Biosynthesis of Oligosaccharides 260

6 Glycobiology 281
6.1 The Glycocalyx 282
6.2 The Lectins 284
6.3 Carbohydrate Microarrays 294
6.4 Glycomimetics and Carbohydrate Drugs 296
6.5 Microbial AdhesionFimH Antagonists and Catch Bonds 308
6.6 The Clinical Impact of Glycobiology 314
6.7 Biochemical Engineering 324
6.8 Glycan Atlassing 333

References 335
In a Nutshell 345
Key Terms 345
Index 347

Thisbe K. Lindhorst is Full Professor at the Faculty of Mathematics and Natural Science of Christiana Albertina University of Kiel (Germany), where she holds a chair in Organic and Biological Chemistry. She studied chemistry at the Universities of München and Münster and received her Ph.D. in Organic Chemistry in 1991 from the University of Hamburg. Her scientific interests are in the field of synthetic organic chemistry and in biological chemistry, especially in glycochemistry and glycobiology. She served as elected president of the German Chemical Society (GDCh) in 2016-2017.