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Full Description
From synthesis to biological function, this widely acclaimed textbook introduces the entire range of modern carbohydrate chemistry and chemical biology. 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 story-telling text boxes providing context within science and society.
"This book is aptly named: it is a well organized, well written presentation of the essentials of carbohydrate chemistry and their relationship to biochemistry." (Journal of Chemical Education)
Contents
1 Structure of saccharides
1.1 Structure of monosaccharides
1.2 Structure of oligosaccharides
1.3 Structure of polysaccharides
1.4 Nomenclature of saccharides
References and key terms
2 Protecting groups for carbohydrates
2.1 Acyl protecting groups
2.2 Ether protecting groups
2.3 Selective protection of the primary hydroxyl group
2.4 Cyclic protecting groups
2.5 Orthoesters as protecting groups
2.6 Protection of the anomeric centre
2.7. One catalyst-one pot protections of per-silylated sugars
2.8 N-Protection for amino sugars
2.9 Enzymes in protecting group chemistry
2.10 Strategic protecting-group sequences on carbohydrate scaffolds
References and key terms
3 O-Glycoside synthesis
3.1 1,2-trans and 1,2-cis Glycosidation
3.2 Factors that influence a glycosylation reaction
3.3 The Koenigs-Knorr method
3.4 Glycosyl acetimidates
3.5 Thioglycosides
3.6 n-Pentenyl glycosides
3.7. Gold?catalysed glycoside synthesis
3.8 Synthesis of 2-deoxy glycosides
3.9 Synthesis of alpha-D-glucosides and beta-D-mannosides
3.10 Synthesis of 2-acetamido-2-deoxy glycosides
3.11 Solid phase oligosaccharide synthesis
3.12 Glycoside synthesis employing enzymes
3.13 Glycosylation strategies
References and key terms
4 Important modifications of the sugar ring
4.1 Activation?substitution reactions at the carbohydrate ring: Deoxyhalo derivatives
4.2 Deoxygenation of carbohydrates
4.3 Epimerisations
4.4 From azido to amino and more: N-functionalised sugars
4.5 Important unsaturated saccharides
4.6 Unexpected journeys of sugars
References and key terms
5 Structure and biosynthesis of glycoconjugates
5.1 Size, diversity, and representation
5.1.1 The actual size of carbohydrates
5.1.2 Structural diversity of oligosaccharides
5.1.3 The symbol representation of carbohydrates
5.2 Structures of glycoconjugates
5.3 Biosynthesis of oligosaccharides
5.3.1 Biosynthesis of N-glycoproteins
5.3.2 Biosynthesis of O-glycoproteins
5.3.3 Biosynthesis of glycosphingolipids
References and key terms
6 Glycobiology
6.1 The glycocalyx
6.2 The lectins
6.3 Carbohydrate microarrays
6.4 Glycomimetics and carbohydrate drugs
6.5 Microbial adhesion - FimH antagonists and catch bonds
6.6 The clinical impact of glycobiology
6.8 Glycan atlassing
References and key terms
