Abstract
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 Mw 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%.
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