Glycotechnology : Synthesis of Carbohydrates and Carbohydrate Mimetics

Abstract

Carbohydrates on cell surfaces play important roles in various cell adhesion processes such as bacterial and viral infection, neurtrophile recruitment, cell differentiation and so on by binding proteins like lectins, antibodies, and glycoenzymes (glycosidases and glycosyltransferases). Carbohydrate analogues which inhibit the interaction between carbohydrates and proteins are promising molecules to clarify and control biological functions of oligosaccharides, and some of the analoges were prepared by using aldolase catalyzed reactions without any tedious procedures. For example, a mimetic of sialyl Lewis X which is an ligand of E-selectin was synthesized by using L-threonine aldolase catalyzed reaction as a key step. In addition, synthetic approach to KDO and 4-azaiduronic acid by using kynureninase and the L-threonine aldolase, respectively, is almost achieved. This review article shows solid phase synthesis and combinatorial synthesis of carbohydrates and treats the details about the utility of aldolases on making carbohydrate mimetics as one of the chemical approaches of glycotechnology.