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

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

Journal Name: Current Organic Chemistry

Volume 16 , Issue 8 , 2012

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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.

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Article Details

VOLUME: 16
ISSUE: 8
Year: 2012
Page: [972 - 977]
Pages: 6
DOI: 10.2174/138527212800194728
Price: $58

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