| Contents AbbreviatiOnS 1 Introduction 2 Structure of saccharides 2.1 Structure ofmonosaccharides 2.2 Structure of simple oligosaccharides 2.3 Structure of p01ysaccharides 2.4 Conformational analysis of saccharides Exercises andproblems 3 Protecting groups for carbohydrates 3.1 Protection of the anomeric center 3.2 Acyl protecting groups 3.3 Ether protecting groups 3.4 Acetal protecting groups 3.5 0rthoesters as protecting groups 3.6 N-Protection for amino sugars 3.7 Enymes in protecting group chemistry 3.8 Carbohydrate scaffolds and orthogonality of protecting groups 3.9 Protecting group patterns for allyl a-d-mannosides Exercises andproblems 4 Important modifications and functionalizatk of the sugar nng 4.1 Activation-substitution reactions at the carbohydrate rin9 4.2 Deoxyhalo derivatives 4.3 Synthesis and reactions of anhydro sugars 4.4 Deoxygenation of carbohydrates 4.5 Functionalization at the anomeric center 4.6 Unsaturated saccharides-Glycals 4.7 Epimerizations 4.8 Carbohydrates as chiral pool materials Exercises andproblems 5 O-Glycoside synthesis 5.1 1,2-trans Glycosidation 5.2 1,2-cis Glycosidation 5.3 Participation of the solvent 5.4 The Koenigs-Knorr method 5.5 The trichloroacetimidate method 5.6 Thioglycosides 5.7 n-Pentenyl glycosides 5.8 Synthesis of2-deoxy glycosides 5.9 Synthesis of[3-mannopyranosides 5.10 Synthesis of 2-deoxy-2-acetamid0-glycopyranosides 5.11 Synthesis of glycopeptides 5.12 Solid phase oligosaccharide synthesis 5.13 Glycoside synthesis employing enzymes 5.14 Glycosylation strategies Exercises andproblems 6 Structure and biosynthesis of gIycoconjugates 6.1 Structural diversity of 01igosaccharides 6.2 Structures of glycoconjugates 6.2.1 Structures of glycoproteins 6.2.2 Structures of glycolipids 6.3 Biosynthesis of 01igosaccharides 6.4 Biosynthesis of N-glycoproteins 6.5 Biosynthesis of O-glycoproteins 6.6 Biosynthesis of 91ycosphingolipids Exercises andproblems 7 Glycobiology 8 Purificatiomn and analysis of carbohydrates 9 the literature of carbohydrate chemistry List of experimental procedures List of tables Subject index |
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