Preferential attack of the (S)-configured ether-linked carbons in bis-(1-chloro-2-propyl) ether by Rhodococcus sp. strain DTB.

Abstract:

:Rhodococcus sp. strain DTB (DSM 44534) was grown on a mixture of (R,R)-, (S,S)- and meso-bis-(1-chloro-2-propyl) ether (BCPE) as the sole source of carbon and energy. During BCPE degradation 1'-chloro-2'-propyl-3-chloro-2-prop-1-enyl-ether (DVE), 1-chloro-2-propanol and chloroacetone intermediates were formed. The BCPE or DVE stereoisomers were metabolized in consecutive order via scission of the ether bond, with discrimination against the (R) configuration. Resting cell suspensions of Rhodococcus pregrown on BCPE showed a preferential attack of the (S)-configured ether-linked carbons, resulting in an enantioselective enrichment of (R,R)-BCPE. Microbial discrimination of BCPE or DVE isomers and chemical conversion of the intermediates to 1-chloro-2-propanol allowed the identification of the configuration of all BCPE isomers and the DVE enantiomers. Elucidation of the absolute configuration of the 1-chloro-2-propanol isomers was achieved by enantioselective chemical synthesis.

journal_name

FEMS Microbiol Ecol

authors

Garbe LA,Moreno-Horn M,Tressl R,Görisch H

doi

10.1111/j.1574-6941.2005.00004.x

subject

Has Abstract

pub_date

2006-01-01 00:00:00

pages

113-21

issue

1

eissn

0168-6496

issn

1574-6941

pii

FEM004

journal_volume

55

pub_type

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