Enantioselective properties of extracellular lipase from Serratia marcescens ES-2 for kinetic resolution of ( S)-flurbiprofen

• Published in: Journal of molecular catalysis. B, Enzymatic Vol. 40; no. 1; pp. 24 - 29
• Main Authors: Bae, Hyun-Ae, Lee, Kwang-Woo, Lee, Yong-Hyun
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier B.V 19.05.2006; Elsevier Science
• Subjects: ( R, S)-Flurbiprofen ethyl ester; ( S)-Flurbiprofen; Bioconversions. Hemisynthesis; Biological and medical sciences; Biotechnology; Fundamental and applied biological sciences. Psychology; Kinetic resolution; Lipase; Methods. Procedures. Technologies; Serratia marcescens ES-2; ( S)-Flurbiprofen; Lipase; Kinetic resolution; ( R, S)-Flurbiprofen ethyl ester; Serratia marcescens ES-2; Enantioselectivity; Enzyme; Triacylglycerol lipase; Esterases; Carboxylic ester hydrolases; Hydrolysis; Ester; (S)-Flurbiprofen; Optical resolution; Serratia marcescens; (R,S)-Hurbiprofen ethyl ester; Bacteria; Hydrolases; Enterobacteriaceae; Flurbiprofen
• ISSN: 1381-1177; 1873-3158
• DOI: 10.1016/j.molcatb.2006.02.004

Serratia marcescens ES-2 excreting a catalytic lipase for the enantioselective hydrolysis of ( R, S)-flurbiprofen ethyl ester to ( S)-flurbiprofen was newly screened, and the excreted lipase was purified by a three-step procedure. The molecular mass was measured to be 64.9 kDa, a relatively high value among known bacterial lipases, and the optimal temperature was determined to be 37 °C. The enantioselectivity was significantly enhanced by the inorganic ion Ca 2+ and surfactant Triton X-207, yet seriously inhibited by EDTA and SDS. The kinetic resolution of 50 mM ( R, S)-flurbiprofen ethyl ester to optically pure ( S)-flurbiprofen was carried out using 100 U lipase/mmol ( R, S)-flurbiprofen ethyl ester in an aqueous phase reaction system supplemented with 10 mM Ca 2+ and 1% Triton X-207. A high conversion, corresponding to an enantiomeric excess of 98.5% and conversion yield of 45.1%, was achieved after 24 h, along with a very high E-value of 332. An enantioselective lipase from S. marcescens ES-2 seems to be practically applicable for the production of optically active ( S)-flurbiprofen.