Biocatalytic synthesis of new copolymers from 3-hydroxybutyric acid and a carbohydrate lactone

Abstract

Abstract Lipase-catalyzed reaction of 3-hydroxybutyric acid with d -glucono-δ-lactone at 5:1 molar ratio and 80 °C yielded a mixture of moderate molecular weight linear and cyclic oligomers. The most efficient biocatalyst, Candida antarctica B lipase (Novozyme 435), allowed the synthesis of new oligomeric compounds with ring-opened gluconolactone units included in the oligomeric chain, without previous derivatization of the sugar, or activation of the acid monomer. The reaction medium nature had an important influence on the product composition. Although the main copolymer amount was synthesized in tert-butanol/dimethylsulfoxide medium, the highest polymerization degrees, up to 9 for the copolymer, and 10 for the 3-hydroxybutyric acid homopolymer co-product, were achieved in solventless conditions.