Enzymatic Derivatization of Saccharides and Their Chemical Polymerization

Article abstract of DOI:10.1016/S0957-4166(00)80231-1

The enzymatic synthesis of sugar-based acetylene and ethylene derivatives as precursors to hydrophilic polymers is described.Propargyl and allyl alcohols have been used as glycosyl acceptors in the transglycosylation reactions of glycosidases with various disaccharides including lactose, maltose, and cellobiose.Reaction of propargyl and allyl alcohols with lactose catalyzed by β-galactosidase resulted in the formation of propargyl-β-D-galalactopyranoside and allyl-β-D-galactopyranoside in 42 and 13percent yields, respectively.Polymerization of propargyl-β-D-galactopyranoside with AlBr3 in ethanol resulted in the formation of oligomeric poly(acetylenic) species (M_w = 1,300).Free radical polymerization of allyl-β-D-galactopyranoside in DMF or water resulted in poly(ethylenic) species with M_w > 30,000.The combined enzymatic and chemical reactions inherent in these syntheses provide a unique approach in the preparation of hydrophilic polymers containing sugars and their derivatives.