Enzymatic Hydrolytic Resolution of Racemic Ibuprofen Ethyl Ester Using an Ionic Liquid as Cosolvent
Abstract
:1. Introduction
2. Results and Discussion
2.1. Effects of ILs
2.2. Conformational Studies of EST
2.3. Effects of IL Concentration
2.4. Effects of Time
2.5. Effects of Temperature
2.6. Effects of pH
2.7. Effects of Substrate Concentration
2.8. Effects of Enzyme Concentration
3. Experimental Section
3.1. Chemicals
3.2. Enzyme Assay
3.3. HPLC Analysis
3.4. CD Spectroscopy
4. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
References
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- Sample Availability: Samples of the compounds are available from the authors.
Ionic Liquids | X (%) | eep (%) | E |
---|---|---|---|
Control | 19.5 | 45.2 | 2.95 |
[Emim][PF6] | 25.3 | 75.4 | 9.1 |
[Bmim][PF6] | 39.2 | 85.6 | 22.4 |
[Hmim][PF6] | 42.1 | 91.2 | 43.3 |
[Omim][PF6] | 43.2 | 93.5 | 63.5 |
[Dmim][PF6] | 44.2 | 94.8 | 84.9 |
[Emim][BF4] | 34.5 | 76.9 | 11.3 |
[Bmim][BF4] | 40.6 | 87.6 | 27.8 |
[Omim][BF4] | 44.9 | 92.3 | 56.9 |
[OmPy][BF4] | 46.5 | 96.2 | 134.7 |
[Bmim][Tf2N] | 44.6 | 95.2 | 94.5 |
[Emim][TfO] | 10.2 | 35.0 | 2.2 |
[Bmim][TfO] | 8.3 | 19.5 | 1.5 |
[Bmim][CH3SO] | 4.3 | 1.4 | 1.0 |
[Omim][CH3SO] | 5.8 | 4.5 | 1.1 |
[Bmim][Cl] | 6.8 | 9.5 | 1.2 |
[Emim][Cl] | 2.3 | 0.6 | 1.0 |
[Omim][Cl] | 3.5 | 3.8 | 1.1 |
[Bmim][NO3] | 34.1 | 82.2 | 15.5 |
[Bmim][CH3COO] | 32.1 | 66.9 | 6.8 |
Ionic Liquids | α-Helix (%) | β-Sheet (%) | β-Turn (%) | Random Coil (%) |
---|---|---|---|---|
Control | 21.5 ± 0.3 | 26.5 ± 0.5 | 35.2 ± 0.2 | 16.8 ± 0.2 |
[Emim][PF6] | 21.3 ± 0.2 | 26.0 ± 0.4 | 36.3 ± 0.2 | 16.4 ± 0.1 |
[Bmim][PF6] | 20.5 ± 0.2 | 27.8 ± 0.3 | 34.7 ± 0.1 | 17.0 ± 0.3 |
[Hmim][PF6] | 19.2 ± 0.5 | 28.9 ± 0.4 | 33.7 ± 0.2 | 17.8 ± 0.1 |
[Omim][PF6] | 18.2 ± 0.2 | 30.7 ± 0.3 | 33.1 ± 0.3 | 18.0 ± 0.2 |
[Dmim][PF6] | 17.9 ± 0.3 | 31.3 ± 0.2 | 32.5 ± 0.4 | 18.3 ± 0.1 |
[Emim][BF4] | 20.5 ± 0.3 | 28.2 ± 0.5 | 34.9 ± 0.1 | 16.4 ± 0.4 |
[Bmim][BF4] | 18.8 ± 0.1 | 30.1 ± 0.3 | 33.7 ± 0.2 | 17.4 ± 0.1 |
[Omim][BF4] | 16.4 ± 0.1 | 31.2 ± 0.5 | 32.2 ± 0.3 | 20.2 ± 0.4 |
[OmPy][BF4] | 15.6 ± 0.2 | 32.3 ± 0.3 | 32.0 ± 0.3 | 20.1 ± 0.4 |
[Bmim][Tf2N] | 16.5 ± 0.3 | 33.0 ± 0.2 | 32.3 ± 0.2 | 18.2 ± 0.3 |
[Emim][TfO] | 22.3 ± 0.6 | 28.2 ± 0.2 | 37.8 ± 0.1 | 11.7 ± 0.3 |
[Bmim][TfO] | 24.9 ± 0.4 | 26.3 ± 0.3 | 39.3 ± 0.2 | 9.5 ± 0.1 |
[Bmim][CH3SO3] | 25.3 ± 0.2 | 25.9 ± 0.4 | 40.3 ± 0.3 | 8.5 ± 0.2 |
[Omim][CH3SO3] | 26.8 ± 0.4 | 26.0 ± 0.2 | 40.1 ± 0.2 | 7.1 ± 0.3 |
[Bmim][Cl] | 25.3 ± 0.2 | 27.2 ± 0.3 | 39.0 ± 0.5 | 8.5 ± 0.2 |
[Emim][Cl] | 25.7 ± 0.1 | 28.3 ± 0.3 | 38.3 ± 0.4 | 7.7 ± 0.5 |
[Omim][Cl] | 26.3 ± 0.2 | 28.5 ± 0.4 | 38.2 ± 0.5 | 7.0 ± 0.3 |
[Bmim][NO3] | 26.5 ± 0.3 | 28.3 ± 0.3 | 39.3 ± 0.1 | 5.9 ± 0.5 |
[Bmim][CH3COO] | 26.3 ± 0.4 | 28.1 ± 0.3 | 39.1 ± 0.2 | 6.5 ± 0.1 |
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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. https://doi.org/10.3390/molecules21070905
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(7):905. https://doi.org/10.3390/molecules21070905
Chicago/Turabian StyleWei, Tao, Kunpeng Yang, Bing Bai, Jie Zang, Xuan Yu, and Duobin Mao. 2016. "Enzymatic Hydrolytic Resolution of Racemic Ibuprofen Ethyl Ester Using an Ionic Liquid as Cosolvent" Molecules 21, no. 7: 905. https://doi.org/10.3390/molecules21070905