Enzymatic Hydrolytic Resolution of Racemic Ibuprofen Ethyl Ester Using an Ionic Liquid as Cosolvent
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 ther...
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MDPI AG
2016-07-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/21/7/905 |
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| author | Tao Wei Kunpeng Yang Bing Bai Jie Zang Xuan Yu Duobin Mao |
| author_facet | Tao Wei Kunpeng Yang Bing Bai Jie Zang Xuan Yu Duobin Mao |
| author_sort | Tao Wei |
| collection | DOAJ |
| description | 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. |
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| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-14T00:30:21Z |
| publishDate | 2016-07-01 |
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| spelling | doaj.art-f9ece469fe5847ca9c5c5a1cbad45f432022-12-21T23:24:52ZengMDPI AGMolecules1420-30492016-07-0121790510.3390/molecules21070905molecules21070905Enzymatic Hydrolytic Resolution of Racemic Ibuprofen Ethyl Ester Using an Ionic Liquid as CosolventTao Wei0Kunpeng Yang1Bing Bai2Jie Zang3Xuan Yu4Duobin Mao5School of Food and Biological Engineering, Zhengzhou University of Light Industry, 5 Dongfeng Rd., Zhengzhou 450002, ChinaSchool of Food and Biological Engineering, Zhengzhou University of Light Industry, 5 Dongfeng Rd., Zhengzhou 450002, ChinaSchool of Food and Biological Engineering, Zhengzhou University of Light Industry, 5 Dongfeng Rd., Zhengzhou 450002, ChinaSchool of Food and Biological Engineering, Zhengzhou University of Light Industry, 5 Dongfeng Rd., Zhengzhou 450002, ChinaSchool of Food and Biological Engineering, Zhengzhou University of Light Industry, 5 Dongfeng Rd., Zhengzhou 450002, ChinaSchool of Food and Biological Engineering, Zhengzhou University of Light Industry, 5 Dongfeng Rd., Zhengzhou 450002, ChinaThe 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.http://www.mdpi.com/1420-3049/21/7/905cosolventenzymaticionic liquidracemic ibuprofen(S)-ibuprofen |
| spellingShingle | Tao Wei Kunpeng Yang Bing Bai Jie Zang Xuan Yu Duobin Mao Enzymatic Hydrolytic Resolution of Racemic Ibuprofen Ethyl Ester Using an Ionic Liquid as Cosolvent Molecules cosolvent enzymatic ionic liquid racemic ibuprofen (S)-ibuprofen |
| title | Enzymatic Hydrolytic Resolution of Racemic Ibuprofen Ethyl Ester Using an Ionic Liquid as Cosolvent |
| title_full | Enzymatic Hydrolytic Resolution of Racemic Ibuprofen Ethyl Ester Using an Ionic Liquid as Cosolvent |
| title_fullStr | Enzymatic Hydrolytic Resolution of Racemic Ibuprofen Ethyl Ester Using an Ionic Liquid as Cosolvent |
| title_full_unstemmed | Enzymatic Hydrolytic Resolution of Racemic Ibuprofen Ethyl Ester Using an Ionic Liquid as Cosolvent |
| title_short | Enzymatic Hydrolytic Resolution of Racemic Ibuprofen Ethyl Ester Using an Ionic Liquid as Cosolvent |
| title_sort | enzymatic hydrolytic resolution of racemic ibuprofen ethyl ester using an ionic liquid as cosolvent |
| topic | cosolvent enzymatic ionic liquid racemic ibuprofen (S)-ibuprofen |
| url | http://www.mdpi.com/1420-3049/21/7/905 |
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