Carbohydrates: The Essential Molecules of Life

This book provides the "nuts and bolts" background for a successful study of carbohydrates - the essential molecules that not only give you energy, but are an integral part of many biological processes.

A question often asked is 'Why do carbohydrate chemistry?' The answer is simple: It is fundamental to a study of biology. Carbohydrates are the building blocks of life and enable biological processes to take place. Therefore the book will provide a taste for the subject of glycobiology.

Covering the basics of carbohydrates and then the chemistry and reactions of carbohydrates this book will enable a chemist to gain essential knowledge that will enable them to move smoothly into the worlds of biochemistry, molecular biology and cell biology.

• includes perspective from new co-author Spencer Williams, who enhances coverage of the connection between carbohydrates and life
• describes the basic chemistry and biology of carbohydrates
• reviews the concepts, synthesis, reactions, and biology of carbohydrates

Researchers, scientists, and advanced undergraduate and graduate students in biochemistry and organic chemistry.

Contents

Preface and Acknowledgements Abbreviations CHAPTER 1: The ‘Nuts and Bolts’ of Carbohydrates The early years The constitution of glucose and other sugars The cyclic forms of sugars, and mutarotation The shape (conformation) of cyclic sugars, and the anomeric effect References CHAPTER 2: Synthesis and Protecting Groups Esters Ethers Acetals The protection of amines Orthogonality References CHAPTER 3: The Reactions of Monosaccharides Oxidation Reduction Halogenation Alkenes and carbocycles Anhydro sugars Deoxy, amino deoxy and branched-chain sugars Miscellaneous reactions Industrially important ketoses Aza and imino sugars References CHAPTER 4: The Formation of the Glycosidic Linkage General Hemiacetals Glycosyl esters Glycosyl halides and orthoesters Glycosyl imidates Thioglycosides Glycosyl sulfoxides Glycals 4-Pentenyl activation Beta-D-Mannopyranosides 2-Acetamido-2-deoxy glycosides 2-Deoxy glycosides Sialosides Furanosides Miscellaneous methods C-Glycosides References CHAPTER 5: Oligosaccharide Synthesis Strategies in oligosaccharide synthesis Polymer-supported synthesis of oligosaccharides References CHAPTER 6: Monosaccharide Metabolism Glucose-6-phosphate: a central molecule in carbohydrate metabolism Glycolysis The fate of pyruvate in primary metabolism Gluconeogenesis The pentose phosphate pathway The glyoxylate cycle Biosynthesis of sugar nucleoside diphosphates Biosynthesis of sialic acids and CMP-sialic acids Biosynthesis of myo-inositol Biosynthesis of L-ascorbic acid References CHAPTER 7: Enzymatic Cleavage of Glycosides: Mechanism, Inhibition and Synthetic Applications Glycoside hydrolases Retaining and inverting mechanisms Unusual enzymes that catalyze glycoside cleavage Transglycosidases Structural-based studies of glycoside hydrolases Reagents and tools for the study of glycoside hydrolases Non-covalent glycoside hydrolase inhibitors Exploitation of glycoside hydrolases in synthesis Glycosynthases: mutant glycosidases for glycoside synthesis Thioglycoligases: mutant glycosidases for thioglycoside synthesis Hehre resynthesis/hydrolysis mechanism References CHAPTER 8: Glycosyltransferases Classification and mechanism Reversibility of glycosyl transfer by glycosyltransferases Inhibitors of glycosyltransferases ‘Direct’ inhibition of glycosyltransferases Therapeutically-useful glycosyltransferase inhibitors ‘Indirect’ inhibition of glycosyltransferases by metabolic interference Chemical modification of glycoconjugates using metabolic pathway promiscuity Exploitation of glycosyltransferases in synthesis References CHAPTER 9: Disaccharides, Oligosaccharides and Polysaccharides Cellobiose and cellulose Starch, amylopectin, beta-amylose and maltose Glycogen Cyclodextrins Sucrose, sucrose analogues and sucrose oligosaccharides Lactose and milk oligosaccharides Fructans Chitobiose, chitin and chitosan Trehalose and trehalose oligosaccharides 1,3-beta-Glucans Mannans References CHAPTER 10: Modifications of Glycans and Glycoconjugates Epimerization Sulfation Phosphorylation Acylation Modifications of sialic acids Other carbohydrate modifications References CHAPTER 11: Glycoproteins and Proteoglycans N-Linked Glycosylation Modification of N-linked glycans for lysosomal targeting O-Linked mucins/proteoglycans, blood group antigens and xenorejection O-Linked N-acetyl-beta-D-glucosamine Glycosylphosphatidylinositol (GPI) membrane anchors Other types of protein glycosylation Proteoglycans and glycosaminoglycans Lysosomal degradation of glycoconjugates References CHAPTER 12: Classics in Carbohydrate Chemistry and Glycobiology The immucillins: transition state analogue inhibitors of enzymic N-ribosyl transfer reactions Development of a candidate anti-toxic malarial vaccine Synthetic carbohydrate anti-tumour vaccines New and improved anticoagulant therapeutics based on heparin

EPILOGUE APPENDIX I Protecting groups APPENDIX II Carbohydrate nomenclature The literature of carbohydrates Reference literature Primary literature Monographs and related works Recent edited works Recent textbooks Miscellaneous
INDEX OF AUTHORS CITED IN THE REFERENCES GENERAL SUBJECT INDEX