Microbial Desaturation of Bis(1‐chloro‐2‐propyl) Ether into a Dichloro Vinyl Ether

Garbe, Leif‐Alexander; Moreno-Horn, Marcus; Rewicki, Dieter; Tressl, Roland; Görisch, Helmut

doi:10.1002/cbic.200300904

Cited by 5 publications

(9 citation statements)

References 15 publications

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“…The reaction mixture contained about 3 mg dry cell weight mL −1 and an initial concentration of 2.5 mM racemic DVE ( rac ‐ 5 ). Mass spectrometry with electron‐impact ionization conditions resulted in the molecular ion at m/z =168 and major fragment ions at m/z =119 ([M−CH 2 Cl] + ), the McLafferty rearrangement product with m/z =92 (base peak, [C 3 H 5 OCl] + ), and m/z =77 ([C 3 H 6 Cl] + ) which is in accordance with the literature (Garbe et al ., 2004). GC, gas chromatography.…”

Section: Resultssupporting

confidence: 90%

“…DVE was chemically synthesized and analysed by 1 H‐ and 13 C‐NMR, as well as by GC/EI‐MS. Detailed information on these syntheses and on spectral data have been reported previously (Moreno‐Horn et al ., 2003; Garbe et al ., 2004). Within 300 min the initial concentration of 2.5 mM rac ‐ 5 was reduced to 0.5 mM.…”

Section: Resultsmentioning

confidence: 99%

“…Pure BCPE stereoisomers cannot be obtained commercially. Racemic ( R / S )‐DVE (DVE rac ‐ 5 ) was synthesized as described previously (Garbe et al ., 2004). ( R )‐(−) epichlorohydrin (( R )‐ 6 ) with a purity of 98.5% was obtained from Fluka (Steinheim, Germany).…”

Section: Methodsmentioning

confidence: 99%

“…Stereoisomeric BCPE 1 was converted to racemic 2‐(2‐chloro‐1‐methylethoxy)propene (CVE, rac ‐ 2 ) by the basic elimination of HCl (potassium tert.‐butoxide in THF) according to the synthesis of DVE ( rac ‐ 5 ) (Garbe et al ., 2004). The structure of CVE ( rac ‐ 2 ) was confirmed by GC/EI‐MS.…”

Section: Methodsmentioning

confidence: 99%

“…Stereoisomeric BCPE 1 was converted to racemic 2-(2chloro-1-methylethoxy)propene (CVE, rac-2) by the basic elimination of HCl (potassium tert.-butoxide in THF) according to the synthesis of DVE (rac-5) (Garbe et al, 2004). The structure of CVE (rac-2) was confirmed by GC/ EI-MS. Electron-impact ionization resulted in the molecular ion M 1 1 at m/z = 134 and showed the expected fragmentation pattern with major fragment ions at m/z = 77 ([C 3 H 6 Cl] 1 ) and the McLafferty rearrangement product with m/z = 58 (base peak, [C 3 H 6 O] 1 ).…”

Section: Hcl Eliminationmentioning

confidence: 99%

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

Garbe¹,

Moreno-Horn²,

Tressl³

et al. 2006

FEMS Microbiology Ecology

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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.

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Section: Resultssupporting

confidence: 90%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Hcl Eliminationmentioning

confidence: 99%

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