Synthesis of chiral epihalohydrins using haloalcohol dehalogenase A from Arthrobacter erithii H10a

Assis, H.M.S. and Bull, Alan T. and Hardman, David J. (1998) Synthesis of chiral epihalohydrins using haloalcohol dehalogenase A from Arthrobacter erithii H10a. Enzyme and Microbial Technology, 22 (7). pp. 545-51. ISSN 0141-0229. (The full text of this publication is not available from this repository)

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Official URL
http://dx.doi.org/10.1016/S0141-0229(97)00255-X

Abstract

Investigation of the epoxide enantiomers formed by the action of the haloalcohol dehalogenase from Arthrobacter erithii H10a revealed that (R)-epichlorohydrin (ECH) was selectively produced from 1,3-dichloro-2-propanol (1,3-DCP). A maximum enantiomeric excess (e.e. > 95%) of (RI-ECH was obtained when dehalogenation of 1,3-DCP occurred in rile presence of an excess of KBr. During the reverse reaction, (R)-ECH was stereoselectively halogenated to form 1,3-DCP of the halogen in the reaction mixture was chloride; however, if chloride was substituted by bromide, the (s)-isomer was halogenated preferentially resulting in the accumulation of the (R)-isomer. (R)-epibromohydrin (EBH) was formed as the result of transhalogenation. If the starting substrates were EBH and KCl, the (R)-isomer was selectively chlorinated while the transhalogenation product was (s)-ECH. (C) 1998 Elsevier Science Inc.

Item Type: Article
Uncontrolled keywords: optically active epihalohydrins; enantioselective dehalogenation; enantioselective halogenation; Arthrobacter erithii H10a; haloalcohol dehalogenase
Subjects: Q Science > QR Microbiology
Divisions: Faculties > Science Technology and Medical Studies > School of Biosciences
Depositing User: I. Ghose
Date Deposited: 04 Apr 2009 10:14
Last Modified: 13 May 2014 13:04
Resource URI: http://kar.kent.ac.uk/id/eprint/17552 (The current URI for this page, for reference purposes)
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