Ultrasound Irradiation Promoted Enzymatic Transesterification of (R/S)-1-Chloro-3-(1-naphthyloxy)-2-propanol
Abstract
:1. Introduction
2. Results and Discussion
2.1. Effect of Enzyme Type
Enzyme | Conventional shaking | Ultrasound irradiation | ||
---|---|---|---|---|
Enzyme activity (μmol·g−1·min−1) | Enantioselectivity ( E value) | Enzyme activity (μmol·g−1·min−1) | Enantioselectivity ( E value) | |
Pseudomonas sp. Lipase (PSL) | 43.3 ± 3.7 | 87 ± 7 | 78.3 ± 3.2 | 98 ± 6 |
Candida antarctica lipase B (CAL-B) | 59.6 ± 2.3 | 70 ± 6 | 85.6 ± 3.1 | 72 ± 8 |
Porcine pancreas lipase (PPL) | 23.7 ± 6.8 | 27 ± 4 | 36.7 ± 1.3 | 21 ± 2 |
Candida sp. 415 lipase (CSL) | 35.6 ± 4.4 | 34 ± 1 | 50.6 ± 2.5 | 36 ± 2 |
Pseudomonas fluorescens lipase (PFL) | 29.8 ± 5.2 | 29 ± 2 | 41.8 ± 1.8 | 37 ± 3 |
2.2. Effect of Ultrasound Power
2.3. Effect of Solvent
Solvent | Log P | Enzyme activity (μmol·g−1·min−1) | Enantioselectivity ( E value) |
---|---|---|---|
Acetonitrile | −0.33 | 10.9 ± 4.2 | 15 ± 2 |
Tetrahydrofuran | 0.49 | 28.7 ± 2.4 | 27 ± 4 |
Cyclohexane | 1.20 | 35.6 ± 3.2 | 53 ± 5 |
Toluene | 2.50 | 61.4 ± 2.6 | 65 ± 3 |
Methyl tert-butyl ether | 2.90 | 69.4 ± 1.3 | 90 ± 5 |
n-Hexane | 3.50 | 78.3 ± 3.2 | 98 ± 6 |
2.4. Effect of Acyl Donor
Acyl donor | Vinyl acetate | Vinyl propionate | Vinyl butyrate | Vinyl valerate | Vinyl caproate |
---|---|---|---|---|---|
Enayzme activity (μmol·g−1·min−1) | 89.6 ± 3.8 | 78.3 ± 3.2 | 66.1 ± 4.1 | 45.2 ± 3.0 | 20.4 ± 2.5 |
Enantioselectivity ( E value) | 69 ± 2 | 98 ± 6 | 81 ± 3 | 73 ± 4 | 70 ± 5 |
2.5. Effect of Temperature
2.6. Substrate Ratio
3. Experimental
3.1. Catalysts and Chemicals
3.2. Enantioselective transesterification of (R/S)-1-chloro-3-(1-naphthyloxy)-2-propanol (3)
3.3. Analytical Methods
4. Conclusions
Acknowledgments
References
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Wang, F.; Zhang, H.; Wang, J.; Chen, G.; Fang, X.; Wang, Z.; Wang, L. Ultrasound Irradiation Promoted Enzymatic Transesterification of (R/S)-1-Chloro-3-(1-naphthyloxy)-2-propanol. Molecules 2012, 17, 10864-10874. https://doi.org/10.3390/molecules170910864
Wang F, Zhang H, Wang J, Chen G, Fang X, Wang Z, Wang L. Ultrasound Irradiation Promoted Enzymatic Transesterification of (R/S)-1-Chloro-3-(1-naphthyloxy)-2-propanol. Molecules. 2012; 17(9):10864-10874. https://doi.org/10.3390/molecules170910864
Chicago/Turabian StyleWang, Feng, Hong Zhang, Jiaxin Wang, Ge Chen, Xuedong Fang, Zhi Wang, and Lei Wang. 2012. "Ultrasound Irradiation Promoted Enzymatic Transesterification of (R/S)-1-Chloro-3-(1-naphthyloxy)-2-propanol" Molecules 17, no. 9: 10864-10874. https://doi.org/10.3390/molecules170910864