Essentials of Carbohydrate Chemistry and Biochemistry

Thisbe Lindhorst is full professor at the Faculty of Mathematics and Natural Science of Christiana Albertina University of Kiel (Germany). She studied chemistry at the Universities of München and Münster, received her diploma in chemistry/biochemistry in 1988 and her Ph.D. in Organic Chemistry in 1991 at the University of Hamburg. After a postdoctoral stay at the University of British Columbia she became Private Docent in 1998 at the University of Hamburg. Since 2000 she holds a chair in Organic and Biological Chemistry in Kiel. Her scientific interests are in the field of synthetic organic chemistry and in biological chemistry, especially in glycochemistry and glycobiology. Current research is focussed on the study of glycosylated surfaces and control of cell adhesion. She is the author of over 150 publications and of the textbook "Essentials in Carbohydrate Chemistry and Biochemistry". She has been an elected member of the DFG Forschungsforum from 2008 to 2016 and served as elected president of the German Chemical Society (GDCh) in 2016-2017.

• 1 Structure of saccharides1.1 Structure of monosaccharides1.2 Structure of oligosaccharides1.3 Structure of polysaccharides1.4 Nomenclature of saccharidesReferences and key terms 2 Protecting groups for carbohydrates2.1 Acyl protecting groups2.2 Ether protecting groups2.3 Selective protection of the primary hydroxyl group2.4 Cyclic protecting groups2.5 Orthoesters as protecting groups2.6 Protection of the anomeric centre2.7. One catalyst-one pot protections of per-silylated sugars2.8 N-Protection for amino sugars2.9 Enzymes in protecting group chemistry2.10 Strategic protecting-group sequences on carbohydrate scaffoldsReferences and key terms 3 O-Glycoside synthesis3.1 1,2-trans and 1,2-cis Glycosidation3.2 Factors that influence a glycosylation reaction3.3 The Koenigs-Knorr method3.4 Glycosyl acetimidates3.5 Thioglycosides3.6 n-Pentenyl glycosides3.7. Gold?catalysed glycoside synthesis3.8 Synthesis of 2-deoxy glycosides3.9 Synthesis of alpha-D-glucosides and beta-D-mannosides3.10 Synthesis of 2-acetamido-2-deoxy glycosides3.11 Solid phase oligosaccharide synthesis3.12 Glycoside synthesis employing enzymes3.13 Glycosylation strategiesReferences and key terms 4 Important modifications of the sugar ring4.1 Activation?substitution reactions at the carbohydrate ring: Deoxyhalo derivatives4.2 Deoxygenation of carbohydrates4.3 Epimerisations4.4 From azido to amino and more: N-functionalised sugars4.5 Important unsaturated saccharides4.6 Unexpected journeys of sugarsReferences and key terms 5 Structure and biosynthesis of glycoconjugates5.1 Size, diversity, and representation5.1.1 The actual size of carbohydrates5.1.2 Structural diversity of oligosaccharides5.1.3 The symbol representation of carbohydrates5.2 Structures of glycoconjugates5.3 Biosynthesis of oligosaccharides5.3.1 Biosynthesis of N-glycoproteins5.3.2 Biosynthesis of O-glycoproteins5.3.3 Biosynthesis of glycosphingolipidsReferences and key terms 6 Glycobiology6.1 The glycocalyx6.2 The lectins6.3 Carbohydrate microarrays6.4 Glycomimetics and carbohydrate drugs6.5 Microbial adhesion - FimH antagonists and catch bonds6.6 The clinical impact of glycobiology6.8 Glycan atlassingReferences and key terms