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Molecules 2016, 21(7), 905; doi:10.3390/molecules21070905

Enzymatic Hydrolytic Resolution of Racemic Ibuprofen Ethyl Ester Using an Ionic Liquid as Cosolvent

1
School of Food and Biological Engineering, Zhengzhou University of Light Industry, 5 Dongfeng Rd., Zhengzhou 450002, China
2
Collaborative Innovation Center of Food Production and Safety, 136 Science Avenue, Zhengzhou 450002, China
*
Author to whom correspondence should be addressed.
Academic Editor: Steven Bull
Received: 12 June 2016 / Revised: 27 June 2016 / Accepted: 7 July 2016 / Published: 13 July 2016
View Full-Text   |   Download PDF [1795 KB, uploaded 13 July 2016]   |  

Abstract

The aim of this study was to develop an ionic liquid (IL) system for the enzymatic resolution of racemic ibuprofen ethyl ester to produce (S)-ibuprofen. Nineteen ILs were selected for use in buffer systems to investigate the effects of ILs as cosolvents for the production of (S)-ibuprofen using thermostable esterase (EST10) from Thermotoga maritima. Analysis of the catalytic efficiency and conformation of EST10 showed that [OmPy][BF4] was the best medium for the EST10-catalyzed production of (S)-ibuprofen. The maximum degree of conversion degree (47.4%), enantiomeric excess of (S)-ibuprofen (96.6%) and enantiomeric ratio of EST10 (177.0) were achieved with an EST10 concentration of 15 mg/mL, racemic ibuprofen ethyl ester concentration of 150 mM, at 75 °C , with a reaction time of 10 h. The reaction time needed to achieve the highest yield of (S)-ibuprofen was decreased from 24 h to 10 h. These results are relevant to the proposed application of ILs as solvents for the EST10-catalyzed production of (S)-ibuprofen. View Full-Text
Keywords: cosolvent; enzymatic; ionic liquid; racemic ibuprofen; (S)-ibuprofen cosolvent; enzymatic; ionic liquid; racemic ibuprofen; (S)-ibuprofen
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Wei, T.; Yang, K.; Bai, B.; Zang, J.; Yu, X.; Mao, D. Enzymatic Hydrolytic Resolution of Racemic Ibuprofen Ethyl Ester Using an Ionic Liquid as Cosolvent. Molecules 2016, 21, 905.

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