An enzymatic approach to combine ring-opening polymerization of epsilo
n-caprolactone and regioselective acylation of methyl glycopyranosides
has been investigated. Candida antarctica lipase B (Novozym 435) cata
lyzed the regiospecific acylation of methyl galacto-and glucopyranosid
e and the ring-opening polymerization of epsilon-caprolactone to give
methyl 6-O-poly(epsilon-caprolactone)glucopyranosides. The synthetic s
trategy led to the synthesis of methyl -poly(epsilon-caprolactone)-bet
a-D-glucopyranoside with a M-w of 3750 and a polydispersity of 1.3. Th
e best results were obtained by drying the system and carrying out the
polymerization at 60 degrees C in bulk, without solvent. The overall
conversion from methyl beta-D-glucopyranoside was 80%.