Carbohydrates: The Essential Molecules of Life

ContentsPreface and AcknowledgementsAbbreviationsCHAPTER 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 ReferencesCHAPTER 2: Synthesis and Protecting Groups Esters Ethers Acetals The protection of amines Orthogonality ReferencesCHAPTER 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 ReferencesCHAPTER 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 ReferencesCHAPTER 5: Oligosaccharide Synthesis Strategies in oligosaccharide synthesisPolymer-supported synthesis of oligosaccharides ReferencesCHAPTER 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 ReferencesCHAPTER 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 ReferencesCHAPTER 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 interferenceChemical modification of glycoconjugates using metabolic pathway promiscuity Exploitation of glycosyltransferases in synthesis ReferencesCHAPTER 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 ReferencesCHAPTER 10: Modifications of Glycans and Glycoconjugates EpimerizationSulfation Phosphorylation Acylation Modifications of sialic acids Other carbohydrate modifications ReferencesCHAPTER 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 ReferencesCHAPTER 12: Classics in Carbohydrate Chemistry and GlycobiologyThe 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 heparinEPILOGUEAPPENDIX I Protecting groupsAPPENDIX 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 REFERENCESGENERAL SUBJECT INDEX