Biocatalytic esterification of β-methylglucoside for synthesis of biocompatible sugar-containing vinyl esters

Biocatalytic synthesis of beta-methylglucoside methacrylate/acrylate by the esterification of beta-methylglucoside with vinyl methacrylate/acrylate was carried out using an immobilized lipase from Candida antarctica (Novozym 435) in organic solvents. Among five model solvents including t-butanol, t-amyl alcohol, acetone, acetonitrile and 1,4-dioxane, t-butanol was found to be an optimal solvent. The amount of 5% (w/v) Novozym 435 resulted in the highest conversion after 48 h, and 1:3 molar ratio of beta-methylglucoside to vinyl methacrylate showed 100% final conversion after 24 h. The optimal initial concentration of beta-methylglucoside and temperature determined front the initial rate and final conversion were observed at 60 g/l and 50 degrees C, respectively. The productivity of sugar esters could be enhanced by the heterogeneous reaction mixture and the addition of beta-methylglucoside after one cycle of reaction in homogeneous reaction. Based on the over 95% of cell viability by MTT assay, produced sugar esters were found to be highly biocompatible. Structural analysis of products was performed by FT-IR and C-13 NMR. (C) 2003 Elsevier B.V. All rights reserved.