Lipase-catalyzed enantioselective acylation of 3-benzyloxypropane-1,2-diol in supercritical carbon dioxide

• Published in: Biochemical engineering journal Vol. 28; no. 3; pp. 275 - 280
• Main Authors: Kmecz, Ildikó, Simándi, Béla, Poppe, László, Juvancz, Zoltán, Renner, Katalin, Bódai, Viktória, Tőke, Enikő R., Csajági, Csaba, Sawinsky, János
• Format: Journal Article
• Language: English
• Published: Lausanne Elsevier B.V 01.03.2006; Amsterdam Elsevier Science; New York, NY
• Subjects: Acylation; Biological and medical sciences; Biotechnology; Enantioselective; Filamentous fungi; Fundamental and applied biological sciences. Psychology; Hypocrea jecorina; Lipase; Supercritical carbon dioxide; Talaromyces; Water activity; Supercritical carbon dioxide; Enantioselective; Water activity; Lipase; Filamentous fungi; Acylation; Water; Diol; Enantioselectivity; Enzyme; Carbon dioxide; Triacylglycerol lipase; Esterases; Supercritical state; Carboxylic ester hydrolases; Fungi; Hydrolases; Thallophyta
• ISSN: 1369-703X; 1873-295X
• DOI: 10.1016/j.bej.2005.11.010

Lipase-catalyzed acylation of 3-benzyloxypropane-1,2-diol with vinyl acetate as acyl donor using different lipases [porcine pancreas lipase (PPL), Lipase AK “Amano”, Lipase PS “Amano”, and crude enzymes from Trichoderma reesei RUT-C30, Thermoascus thermophilus (NRRL5208), Talaromyces emersonii (NRLL3221)] was studied in supercritical carbon dioxide (scCO 2). In the reactions catalyzed by different lipases different amounts of monoacetate and diacetate products along with minor amounts of cyclic acetals forming from the diol and acetaldehyde were obtained. Application of Lipase AK led to the highest conversion (84.7%) and the highest enantiomeric excess values (ee monoacetates = 38%, ee diacetate = 85%). Effect of water content of scCO 2 on the productivity and the enantiomer selectivity of the reactions with Lipase AK was also investigated.