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

• Published in: Chemical engineering journal (Lausanne, Switzerland : 1996) Switzerland : 1996), 2004-05, Vol.99 (1), p.15-22
• Main Authors: Kim, Jiseok, Haam, Seungjoo, Park, Dae-Won, Ahn, Ik-Sung, Lee, Tai Gyu, Kim, Hae-Sung, Kim, Woo-Sik
• Format: Article
• Language: English
• Subjects: Applied sciences; Biological and medical sciences; Biotechnology; Chemical engineering; Exact sciences and technology; Fundamental and applied biological sciences. Psychology; Methods. Procedures. Technologies; MTT assay; Novozym 435; Others; Various methods and equipments; Vinyl acrylate; Vinyl methacrylate; β-Methylglucoside
• ISSN: 1385-8947; 1873-3212
• DOI: 10.1016/j.cej.2003.09.001

Biocatalytic synthesis of β-methylglucoside methacrylate/acrylate by the esterification of β-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 β-methylglucoside to vinyl methacrylate showed 100% final conversion after 24 h. The optimal initial concentration of β-methylglucoside and temperature determined from the initial rate and final conversion were observed at 60 g/l and 50 °C, respectively. The productivity of sugar esters could be enhanced by the heterogeneous reaction mixture and the addition of β-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 13 C NMR.