Please use this identifier to cite or link to this item:
https://doi.org/10.1016/j.tetasy.2007.12.019
DC Field | Value | |
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dc.title | Preparation of (S)-2-, 3-, and 4-chlorostyrene oxides with the epoxide hydrolase from Sphingomonas sp. HXN-200 | |
dc.contributor.author | Jia, X. | |
dc.contributor.author | Wang, Z. | |
dc.contributor.author | Li, Z. | |
dc.date.accessioned | 2014-06-17T07:47:24Z | |
dc.date.available | 2014-06-17T07:47:24Z | |
dc.date.issued | 2008-03-04 | |
dc.identifier.citation | Jia, X., Wang, Z., Li, Z. (2008-03-04). Preparation of (S)-2-, 3-, and 4-chlorostyrene oxides with the epoxide hydrolase from Sphingomonas sp. HXN-200. Tetrahedron Asymmetry 19 (4) : 407-415. ScholarBank@NUS Repository. https://doi.org/10.1016/j.tetasy.2007.12.019 | |
dc.identifier.issn | 09574166 | |
dc.identifier.uri | http://scholarbank.nus.edu.sg/handle/10635/64454 | |
dc.description.abstract | The epoxide hydrolase from Sphingomonas sp. HXN-200 catalyzed the enantioselective hydrolysis of racemic 2-, 3-, and 4-chlorostyrene oxides 1-3 to form the corresponding (R)-diols and gave the (S)-epoxides 1-3 in high ee. The reactions were examined with frozen/thawed cells as well as cell-free extracts of Sphingomonas sp. HXN-200 as catalysts in an aqueous, and a two-liquid phase system, respectively. Biotransformation in the two-liquid phase system containing n-hexane as an organic phase showed a higher enantioselectivity than that in the single aqueous phase, due to the reduced non-enzymatic hydrolysis. Hydrolysis of 60 mM 2-chlorostyrene oxide 1 gave 31.3% of (S)-2-chlorostyrene oxide 1 in 98.8% ee with an enantioselectivity factor (E) of 12; hydrolysis of 100 mM 4-chlorostyrene oxide 3 afforded 30.8% of (S)-4-chlorostyrene oxide 3 with 98.6% ee with an E-value of 11. The best results were obtained with the hydrolysis of 3-chlorostyrene oxide 2: biotransformation with 100 mM substrate gave 44.0% of (S)-3-chlorostyrene oxide 2 in 99.0% ee with an E-value of 41; such enantioselectivity is much higher than that of any other known epoxide hydrolases for this reaction; preparative biotransformation demonstrated the efficient synthesis of (S)-3-chlorostyrene oxide 2, an intermediate for the preparation of an IGF-1R kinase inhibitor BMS-536924, with 99.1% ee and 41% isolated yield. © 2008 Elsevier Ltd. All rights reserved. | |
dc.description.uri | http://libproxy1.nus.edu.sg/login?url=http://dx.doi.org/10.1016/j.tetasy.2007.12.019 | |
dc.source | Scopus | |
dc.type | Article | |
dc.contributor.department | CHEMICAL & BIOMOLECULAR ENGINEERING | |
dc.description.doi | 10.1016/j.tetasy.2007.12.019 | |
dc.description.sourcetitle | Tetrahedron Asymmetry | |
dc.description.volume | 19 | |
dc.description.issue | 4 | |
dc.description.page | 407-415 | |
dc.description.coden | TASYE | |
dc.identifier.isiut | 000255350500003 | |
Appears in Collections: | Staff Publications |
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