Application of Lipases from Candida rugosa in the Enantioselective Esterification of (R,S)-Ibuprofen

Title:Application of Lipases from Candida rugosa in the Enantioselective Esterification of (R,S)-Ibuprofen

Volume: 16 Issue: 8

Author(s): Tomasz Siodmiak, Jan K. Ruminski and Michal P. Marszall

Affiliation:

Keywords: Esterification, Biocatalytic reaction, Resolution, (R, S)-ibuprofen, Candida rugosa lipase.

Abstract: Three commercially available lipases from Candida rugosa (OF and MY from Meito Sangyo Co., and CRL from Sigma- Aldrich Co.) were used for the enantioselective esterification reaction of (R,S)-ibuprofen with 1-propanol and 2-propanol in saturated cyclohexane as reaction medium. All tested lipases preferentially catalysed the esterification of the S-enantiomer of ibuprofen. However, each one of the analysed lipases demonstrated differences in the catalytic activity. Lipase OF showed the highest conversion degree, and the best enantioselectivity was observed for MY and CRL lipases. The influence of temperature, reaction time and addition of N,N’- dicyclohexylcarbodiimide (DCC) on the enantioselectivity and on the conversion degree in the enzymatic esterification was studied and the optimal condition for enantioselective esterification was evaluated. Moreover, the application of new commercial cellulose-based tris(3,5-dimethylphenylcarbamate) HPLC chiral column was demonstrated for effective separation, qualification and quantification of both substrates and products within one chromatographic analysis.

Cite this article as:

Siodmiak Tomasz, K. Ruminski Jan and P. Marszall Michal, Application of Lipases from Candida rugosa in the Enantioselective Esterification of (R,S)-Ibuprofen, Current Organic Chemistry 2012; 16 (8) . https://dx.doi.org/10.2174/138527212800194728