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. Introduction 2. Structure of saccharides2.1 Structure of monosaccharides2.2 Structure of simple oligosaccharides2.3 Structure of polysaccharides2.4 Conformational analysis of saccharidesChapter summaryExercises and problems 3 Protecting groups for carbohydrates3.1 Protection of the anomeric center3.2 Acyl protecting groups3.3 Ether protecting groups3.4 Acetal protecting groups3.5 Orthoesters as protecting groups3.6 N-Protection for amino sugars3.7 Enzymes in protecting group chemistry3.8 Carbohydrate scaffolds and orthogonality of protecting groups3.9 Protecting group patterns for allyl alpha-D-mannosidesChapter summaryExercises and problems 4. Important modifications and functionalizations of the sugar ring4.1 Activation-substitution reactions at the carbohydrate ring4.2 Deoxyhalo derivatives4.3 Synthesis and reactions of anhydro sugars4.4 Deoxygenation of carbohydrates4.5 Functionalization at the anomeric center4.6 Unsaturated saccharides -Glycals4.7 Epimerizations4.8 Carbohydrates as chiral pool materialsChapter summaryExercises and problems 5 O-Glycoside synthesis5.1 1,2-trans Glycosidation5.2 1,2-cis Glycosidation5.3 Participation of the solvent5.4 The Koenigs-Knorr method5.5 The trichloroacetimidate method5.6 Thioglycosides5.7 n-Pentenyl glycosides5.8 Synthesis of 2-deoxy glycosides5.9 Synthesis of beta-mannopyranosides5.10 Synthesis of 2-deoxy-2-acetamido-glycopyranosides5.11 Synthesis of glycopeptides5.12 Solid phase oligosaccharide synthesis5.13 Glycoside synthesis employing enzymes5.14 Glycosylation strategiesChapter summaryExercises and problems 6 Structure and biosynthesis of glycoconjugates6.1 Structural diversity of oligosaccharides6.2 Structures of glycoconjugates6.3 Biosynthesis of oligosaccharides6.4 Biosynthesis of N-glycoproteins6.5 Biosynthesis of O-glycoproteins6.6 Biosynthesis of glycosphingolipidsChapter summaryExercises and problems 7. Glycobiology7.1 Essentials of Glycobiology7.2 Blood group specificities7.3 Lectins7.4 Oligosaccharide epitopes critical in cell biology7.5 Understanding of the molecular interactions of the glycocalyx7.6 Biochemical engineering7.7 Metabolic oligosaccharide engineering7.9 Microbial adhesion7.10 Carbohydrate drugsChapter summaryExercises and problems 8. Glycoarrays and Glycomimetics8.1 Glycoarrays8.2 Glycomimetics8.3 Bacterial Anti-adhesivesChapter summaryExercises and problems