Please use this identifier to cite or link to this item: https://doi.org/10.1016/j.tetasy.2007.12.019
DC FieldValue
dc.titlePreparation of (S)-2-, 3-, and 4-chlorostyrene oxides with the epoxide hydrolase from Sphingomonas sp. HXN-200
dc.contributor.authorJia, X.
dc.contributor.authorWang, Z.
dc.contributor.authorLi, Z.
dc.date.accessioned2014-06-17T07:47:24Z
dc.date.available2014-06-17T07:47:24Z
dc.date.issued2008-03-04
dc.identifier.citationJia, 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.issn09574166
dc.identifier.urihttp://scholarbank.nus.edu.sg/handle/10635/64454
dc.description.abstractThe 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.urihttp://libproxy1.nus.edu.sg/login?url=http://dx.doi.org/10.1016/j.tetasy.2007.12.019
dc.sourceScopus
dc.typeArticle
dc.contributor.departmentCHEMICAL & BIOMOLECULAR ENGINEERING
dc.description.doi10.1016/j.tetasy.2007.12.019
dc.description.sourcetitleTetrahedron Asymmetry
dc.description.volume19
dc.description.issue4
dc.description.page407-415
dc.description.codenTASYE
dc.identifier.isiut000255350500003
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