Lipase-Catalyzed Synthesis of Methyl 6-O-Poly(ε-caprolactone)glycopyranosides

An enzymatic approach to combine ring-opening polymerization of ε-caprolactone and regioselective acylation of methyl glycopyranosides has been investigated. Candida antarctica lipase B (Novozym 435) catalyzed the regiospecific acylation of methyl galacto- and glucopyranoside and the ring-opening polymerization of ε-caprolactone to give methyl 6- O -poly(ε-caprolactone)glycopyranosides. The synthetic strategy led to the synthesis of methyl 6- O -poly(ε-caprolactone)-β- d -glucopyranoside with a M w of 3750 and a polydispersity of 1.3. The best results were obtained by drying the system and carrying out the polymerization at 60 °C in bulk, without solvent. The overall conversion from methyl β- d -glucopyranoside was 80%.