The Molecular and Supramolecular Chemistry of Carbohydrates Chemical Introduction to the Glycosciences

by David, Serge; Beau, Rosemary Green

• ISBN13: 9780198500476
• ISBN10: 0198500475
• Format: Hardcover
• Copyright: 1998-01-08
• Publisher: Oxford University Press

Summary

There is currently a great deal of interest in carbohydrate research amongchemists and biologists, in both academic and industrial laboratories. Onereason is the involvement of oligosaccharide molecules in many recognitionphenomena in the living world. Another reason is the growing demand for chiralsynthesissugars are an amazingly cheap source of chirality but must beefficiently processed. Thirdly the role of conformation in carbohydrateinteractions has stimulated much experimental and theoretical work. There arecausal links between advances in each of these fields, from molecular orbitalsto immunochemistry, so that no research worker in his narrow specialisation canafford to ignore what is going on elsewhere. Thus a body of knowledge has beenbuilt from what is now called the 'glycosciences'. This book attempts todescribe glycosciences in their true perspective. Organic chemistry is thebackbone of the presentation, but carbohydrate chemistry offers a wealth ofsupramolecular associations. This book is unique, among similar texts oncarbohydrates, in that half its content is devoted to the description ofimportant examples of such interactions. The opening chapters deal with theproblems of configuration, conformation, derivatization, and modifications ofmonosaccharides, with examples on their utilization in total synthesis. Theanomeric effectthe most popular of all stereoelectronic effects, and a gift tocarbohydrate chemists and chemists in generalis discussed at length. Thefollowing chapters deal with oligosaccharides; the essentials of enzymicsynthesis, with its high performances; and the sialic acids, which are at theforefront of carbohydrate research. The author describes recognition reactions,including blood group phenomena, interactions involving sialic acids, the activesite of heparin, tumour markers, and selectins. The association of sugars withsmall molecules, notably with inorganic species, is the subject of anotherchapter. Throughout the book, great attention has been given to practicaldetails especially in the description of experiments involving unfamiliartechniques. Many tables, figures, diagrams, experimental protocols and a surveyof the literature up to March 1996 will help the reader to understand thesalient facts and visualize a broad spectrum of ideas.

Table of Contents

1. Configuration of monosaccharides	1	(16)
2. Conformation of monosaccharides and their derivatives	17	(25)
3. Alkyl and aryl glycosides and glycosamines	42	(25)
4. Nomenclature	67	(10)
5. Reactions of hydroxyl groups	77	(19)
6. Reactions of carbonyl groups and hemiacetals	96	(13)
7. Changes of configuration, unsaturated and branched-chain sugars	109	(19)
8. Sugars in chiral synthesis	128	(15)
9. Oligosaccharides: configuration and analysis	143	(19)
10. Chemical transformations and synthesis of oligosaccharides	162	(24)
11. Associations with anions, cations, and inorganic molecules	186	(22)
12. Sialic acids and sialylated oligosaccharides	208	(16)
13. Glycoconjugates	224	(15)
14. Structure of some crystallized sugar-protein complexes	239	(11)
15. Antigens and antibodies. Lectins	250	(15)
16. ABH and related blood group antigens	265	(12)
17. Important recognition events involving oligosaccharides in the living world	277	(19)
18. Oligosaccharides as ligands to DNA	296	(15)
Index	311