Chapter 9 - Oligosaccharide Synthesis

Abstract

The chapter begins by discussing strategies in oligosaccharide synthesis. Linear syntheses methods are first considered. A linear synthesis is one in which a monosaccharide by the successive addition of other monosaccharides is transformed into an oligosaccharide. Convergent syntheses, which assembles the oligosaccharide from smaller, preformed components is also discussed. Two-directional synthesis is described revealing Boons' report that a monosaccharide derivative is constructed such that it is capable of acting as a glycosyl donor and acceptor. “One-pot” synthesis, the step-wise addition of building blocks to the growing chain, is detailed. Polymer-supported synthesis of oligosaccharides, types of polymers, linkers, the attachment of the sugar to the polymer, the glycosyl donors used, insoluble versus soluble polymers, and combinational synthesis and the generation of “libraries” are the other concepts discussed. Enzyme-catalyzed glycoside synthesis, glycosyl transferases and hydrolases, classification of glycosidases, the mechanism of action of glycosidases, glycoside synthesis using “glycosynthases” and other methods are described. Other general matters concerning carbohydrate processing enzymes are discussed.