ENZYMATIC DERIVATIZATION OF SACCHARIDES AND THEIR CHEMICAL POLYMERIZATION

The enzymatic synthesis of sugar-based acetylene and ethylene derivati ves as precursors to hydrophilic polymers is described. Propargyl and allyl alcohols have been used as glycosyl acceptors in the transglycos ylation reactions of glycosidases with various disaccharides including lactose, maltose, and cellobiose. Reaction of propargyl and allyl alc ohols with lactose catalyzed by beta-galactosidase resulted in the for mation of propargyl-beta-D-galactopyranoside and allyl-beta-D-galactop yranoside in 42 and 13% yields, respectively. Polymerization of propar gyl-beta-D-galactopyranoside with AlBr3 in ethanol resulted in the for mation of oligomeric poly(acetylenic) species (M(W) = 1,300). Free rad ical polymerization of allyl-beta-D-galactopyranoside in DMF or water resulted in poly(ethylenic) species with M(W) > 30,000. The combined e nzymatic and chemical reactions inherent in these syntheses provide a unique approach in the preparation of hydrophilic polymers containing sugars and their derivatives.