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.
Keywords: Esterification, Biocatalytic reaction, Resolution, (R, S)-ibuprofen, Candida rugosa lipase.
Current Organic Chemistry
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.
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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
DOI https://dx.doi.org/10.2174/138527212800194728 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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