CALB Immobilized onto Magnetic Nanoparticles for Efficient Kinetic Resolution of Racemic Secondary Alcohols: Long-Term Stability and Reusability
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemical Characterization and Analysis
2.2. Optimal Conditions for the Preparation of Immobilized CALB
2.3. Optimal Conditions for the Resolution of 1-Phenylethanol
2.4. Reusability of Magnetic CALB CLEAs
2.5. Storage Stability of Magnetic CALB CLEAs
2.6. Kinetic Resolution of Different Secondary Alcohols
3. Materials and Methods
3.1. Materials
3.2. Expression of CALB
3.3. Preparation of Modified Magnetic Fe3O4 Nanoparticles
3.4. Preparation of CALB CLEAs and Magnetic CLEAs of CALB
3.5. Activity Assay
3.6. Calculation
3.7. Characterization
3.7.1. FTIR
3.7.2. SEM
3.7.3. HPLC
3.7.4. 1H-NMR
3.8. Optimization for Magnetic CALB CLEAs Preparation
3.9. 1-Phenylethanol Resolution Reusability
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Samples of the compounds are not available from the authors. |
Solvents | Log P b | eep% | ees% | C% | E |
---|---|---|---|---|---|
1,4-Dioxane | −1.1 | 38 | 3 | 5.9 | 2 |
Acetonitrile | −0.33 | >99 | 3 | 3.2 | 206 |
Isopropanol | 0.25 | >99 | 1.4 | 1.4 | 202 |
Tetrahydrofuran | 0.46 | >99 | 5.4 | 5.2 | 210 |
Methyl tert-butyl ether | 0.96 | >99 | 42 | 29.9 | 300 |
Isopropyl ether | 1.9 | >99 | 46 | 31.8 | 316 |
Toluene | 2.5 | >99 | 56 | 36.2 | 351 |
Hexane | 3.5 | >99 | 88 | 47.1 | 587 |
Heptane | 4.0 | >99 | 85 | 46 | 546 |
Isooctane | 4.5 | >99 | 78 | 44.0 | 478 |
Entry | Substrate | Catalyst | eep b(%) | ees b(%) | Conversion b (%) | E |
---|---|---|---|---|---|---|
1 | Magnetic CALB CLEAs | >99 | >99 | 50.0 | >1000 | |
Novozym 435 | 96 | >99 | 51.1 | 175 | ||
Free CALB | >99 | 2 | 2.1 | 204 | ||
Fe3O4 | >99 | 1 | 1.3 | 203 | ||
APTES–Fe3O4 | >99 | 2 | 1.9 | 204 | ||
2 | Magnetic CALB CLEAs | >99 | 94 | 48.4 | >1000 | |
Novozym 435 | 94 | 98 | 50.9 | 149 | ||
3 | Magnetic CALB CLEAs | 95 | 43 | 31.0 | 56 | |
Novozym 435 | 35 | 74. | 68.1 | 4 | ||
4 | Magnetic CALB CLEAs | 94 | 28 | 22.6 | 43 | |
Novozym 435 | 30 | 98 | 76.3 | 7 | ||
5 | Magnetic CALB CLEAs | >99 | >99 | 50.0 | >1000 | |
Novozym 435 | 8 | >99 | 92.1 | 4 | ||
6 | Magnetic CALB CLEAs | 95 | 7 | 7.1 | 39 | |
Novozym 435 | 97 | 63 | 39.2 | 128 | ||
7 | Magnetic CALB CLEAs | / | 0 | 0 | / | |
Novozym 435 | >99 | <1 | 0.6 | 200 | ||
8 | Magnetic CALB CLEAs | 92 | 22 | 19.4 | 31 | |
Novozym 435 | 91 | >99 | 52.1 | 109 | ||
9 | Magnetic CALB CLEAs | >99 | 83 | 45.5 | 605 | |
Novozym 435 | 95 | >99 | 51.0 | 207 | ||
10 | Magnetic CALB CLEAs | >99 | >99 | 50.0 | >1000 | |
Novozym 435 | 94 | >99 | 51.4 | 160 | ||
11 | Magnetic CALB CLEAs | >99 | 78 | 44.0 | 472 | |
Novozym 435 | >99 | >99 | 50.0 | >1000 | ||
12 | Magnetic CALB CLEAs | >99 | 25 | 20.1 | 254 | |
Novozym 435 | >99 | >99 | 50.0 | >1000 | ||
13 | Magnetic CALB CLEAs | >99 | >99 | 50.0 | >1000 | |
Novozym 435 | >99 | >99 | 49.8 | >1000 | ||
14 | Magnetic CALB CLEAs | >99 | >99 | 50.0 | >1000 | |
Novozym 435 | 97 | >99 | 50.7 | 374 | ||
15 | Magnetic CALB CLEAs | >99 | >99 | 50.0 | >1000 | |
Novozym 435 | 95 | 2.8 | 2.8 | 45 |
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Xing, X.; Jia, J.-Q.; Zhang, J.-F.; Zhou, Z.-W.; Li, J.; Wang, N.; Yu, X.-Q. CALB Immobilized onto Magnetic Nanoparticles for Efficient Kinetic Resolution of Racemic Secondary Alcohols: Long-Term Stability and Reusability. Molecules 2019, 24, 490. https://doi.org/10.3390/molecules24030490
Xing X, Jia J-Q, Zhang J-F, Zhou Z-W, Li J, Wang N, Yu X-Q. CALB Immobilized onto Magnetic Nanoparticles for Efficient Kinetic Resolution of Racemic Secondary Alcohols: Long-Term Stability and Reusability. Molecules. 2019; 24(3):490. https://doi.org/10.3390/molecules24030490
Chicago/Turabian StyleXing, Xiu, Jun-Qi Jia, Jing-Fan Zhang, Zi-Wen Zhou, Jun Li, Na Wang, and Xiao-Qi Yu. 2019. "CALB Immobilized onto Magnetic Nanoparticles for Efficient Kinetic Resolution of Racemic Secondary Alcohols: Long-Term Stability and Reusability" Molecules 24, no. 3: 490. https://doi.org/10.3390/molecules24030490