Enzymatic glycoside synthesis

Kittl, R. and Withers, S.G. (2010) New approaches to enzymatic glycoside synthesis through directed evolution. Carbokydr. Res., 345, 1272 1279. 

Enzymatic approaches to glycoside synthesis may circumvent these problems. Enzymes (i.e. nucleoside glycosyl transferases) are stereospecific and regioselective catalyzing glycosyl transfer reaction under mild conditions. Extensive protection-deprotection schemes are unnecessary and the control of anomeric configuration is managed. 

Accqitor glycosides, synthesis, 54,56 Acceptor polymers, use in enzymatic syndiesis of oligosacdiarides, 90-97 Acetate kinase, use for ATP regeneration, 112,114,115/... 

Much of the chemistry of monosaccharides is the familiar chemistry of alcohols and aldehydes/ketones. Thus, the hydroxyl groups of carbohydrates form esters and ethers. The carbonyl group of a monosaccharide can be reduced with NaBH4 to form an alditol, oxidized with aqueous Br2 to form an aldonic acid, oxidized with HNO3 to form an aldaric acid, oxidized enzymatically to form a uronic acid, or treated with an alcohol in the presence of acid to form a glycoside. Monosaccharides can also be chain-lengthened by the multistep Kiliani-Fischer synthesis and can be chain-shortened by the Wohl degradation. 

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