Please use this identifier to cite or link to this item:
Title: Preparation of (S)-2-, 3-, and 4-chlorostyrene oxides with the epoxide hydrolase from Sphingomonas sp. HXN-200
Authors: Jia, X.
Wang, Z. 
Li, Z. 
Issue Date: 4-Mar-2008
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.
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.
Source Title: Tetrahedron Asymmetry
ISSN: 09574166
DOI: 10.1016/j.tetasy.2007.12.019
Appears in Collections:Staff Publications

Show full item record
Files in This Item:
There are no files associated with this item.


checked on Oct 20, 2021


checked on Oct 20, 2021

Page view(s)

checked on Oct 14, 2021

Google ScholarTM



Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.