Essentials of Carbohydrate Chemistry and Biochemistry

Thoroughly updated edition of the leading textbook on carbohydrate chemistry From synthesis to biological function, Essentials of Carbohydrate Chemistry and Biochemistry introduces the entire range of modern carbohydrate chemistry and chemical biology. In this new edition, the increasing recognition of the role of carbohydrates in biology, pharmacology, and medicine is reflected in greatly expanded sections on glycobiology and glycomimetics. The new edition also features a new set of illustrations, many of which are now in color, as well as intriguing practical examples and story-telling text boxes providing context for the relevance of carbohydrates in science and society. Didactically written by an experienced lecturer and graduate student advisor, Essentials of Carbohydrate Chemistry and Biochemistry includes information on: - Protecting groups for carbohydrates, including protection of the anomeric center, acyl, ether, and acetal protecting groups - Methods for the analysis of carbohydrates, covering polarimetry, NMR spectroscopy, and mass spectrometry - Important modifications and functionalizations of the sugar ring, such as deoxy derivatives, anhydro sugars, and epimerizations - Principal approaches to the chemical and enzymatic synthesis of glycosides and glycopeptides, and modern examples of advancing the art of glycoside synthesis employing solution as well as solid phase methods - Structural diversity and biosynthesis of oligosaccharides and glycoconjugates - A greatly expanded section on glycobiology that focuses on the role of carbohydrates in membrane architecture, cell-cell-recognition. cell adhesion, and their biomedical applications Updated and thoroughly modernized for more efficient classroom teaching and self-learning, the Fourth Edition of Essentials of Carbohydrate Chemistry and Biochemistry is essential reading for students in chemistry, biochemistry, biotechnology, and pharmacy with an interest in glycochemistry and glycobiology.

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.

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-Catalyst-One-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 Koenigs-Knorr 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 ß-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 Activation-Substitution 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 Adhesion--FimH 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