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Application of green chemistry in decreasing adverse effect of (R,S)-ibuprofen
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Abstract
Lipases from Candida rugosa (OF and MY) were tested for their application in the enzymatic kinetic resolution of (R,S)-ibuprofen by enantioselective esterification. In this study, screening of enzymes was performed, and lipase MY was selected as an optimal catalyst, which allows to obtain products with high enantiopurity. Additionally, the influence of reaction time on the enantiomeric ratio and conversion was tested. High values of enantiomeric ratio (E in the range of 40.1–71.3) of the esterification of (R,S)- -ibuprofen were obtained using lipase MY, which has a great significance in the field of pharmaceutical synthesis of drugs. The chiral compounds (substrates and products) were analysed with the use of chiral stationary phases. As a result of the optimization, the reaction performed with the application of lipase MY allowed to achieve less toxic for human health (S)-enantiomer of ibuprofen with the high enantiomeric excess of product eep = 95%. Conversion of the reaction was c = 30.6% and enantioselectivity E = 58.9 after 126 h of incubation.
Abstract
Lipases from Candida rugosa (OF and MY) were tested for their application in the enzymatic kinetic resolution of (R,S)-ibuprofen by enantioselective esterification. In this study, screening of enzymes was performed, and lipase MY was selected as an optimal catalyst, which allows to obtain products with high enantiopurity. Additionally, the influence of reaction time on the enantiomeric ratio and conversion was tested. High values of enantiomeric ratio (E in the range of 40.1–71.3) of the esterification of (R,S)- -ibuprofen were obtained using lipase MY, which has a great significance in the field of pharmaceutical synthesis of drugs. The chiral compounds (substrates and products) were analysed with the use of chiral stationary phases. As a result of the optimization, the reaction performed with the application of lipase MY allowed to achieve less toxic for human health (S)-enantiomer of ibuprofen with the high enantiomeric excess of product eep = 95%. Conversion of the reaction was c = 30.6% and enantioselectivity E = 58.9 after 126 h of incubation.
Keywords
Candida rugosa lipase, green chemistry, (R,S)-ibuprofen, kinetic resolution
About this articleTitle
Application of green chemistry in decreasing adverse effect of (R,S)-ibuprofen
Journal
Issue
Article type
Original article
Pages
55-61
Published online
2015-07-14
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776
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1791
Bibliographic record
Folia Medica Copernicana 2015;3(2):55-61.
Keywords
Candida rugosa lipase
green chemistry
(R
S)-ibuprofen
kinetic resolution
Authors
Joanna Siódmiak
Tomasz Siódmiak
Michał Falkowski
Adam Sikora
Michał Piotr Marszałł