Synthesis of optically pure 1,2-epoxypropane by microbial asymmetric reduction of chloroacetone

Weijers, C.A.G.M.; Litjens, Mike J. J.; Bont, J.A.M. de

doi:10.1007/bf00170075

Cited by 17 publications

(4 citation statements)

References 24 publications

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“…In addition, a number of micro‐organisms are capable of reducing haloketones to their corresponding chlorinated alcohols by the action of alcohol dehydrogenases. Weijers et al . (1992) reported the asymmetric reduction of chloroacetone into ( S )‐1‐chloro‐2‐propanol by the yeast Rhodotorula glutinis .…”

Section: Discussionmentioning

confidence: 99%

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: Discussionmentioning

confidence: 99%

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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“…Although acetone might undergo some degradation during this initial 90 min, it is very unlikely that 650 nmol of acetone could have been produced and consumed during this time period, given the slow initial rate at which 1,000 nmol of acetone was degraded by the same concentration of propylene-grown cells as was used in the epichlorohydrin degradation assays. A number of microorganisms are capable of reducing haloketones to the corresponding chlorinated alcohols by the action of alcohol dehydrogenases (30). Xanthobacter strain Py2 cultured with isopropanol as the carbon source has been shown to reduce chloroacetone to 1-chloro-2-propanol in this manner (30).…”

Section: Discussionmentioning

confidence: 99%

“…A number of microorganisms are capable of reducing haloketones to the corresponding chlorinated alcohols by the action of alcohol dehydrogenases (30). Xanthobacter strain Py2 cultured with isopropanol as the carbon source has been shown to reduce chloroacetone to 1-chloro-2-propanol in this manner (30). In our studies of epichlorohydrin metabolism, we did not detect 1-chloro-2-propanol as a product of chloroacetone degradation, but we did chemically convert chloroacetone to 1-chloro-2-propanol by reduction with NaBH 4 to confirm the identity of the chloroacetone product.…”

Section: Discussionmentioning

confidence: 99%

Characterization of a new pathway for epichlorohydrin degradation by whole cells of xanthobacter strain py2

Small¹,

Tilley²,

Ensign³

1995

Appl Environ Microbiol

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The degradation of epichlorohydrin (3-chloropropylene oxide or 1-chloro-2,3-epoxypropane) by whole-cell suspensions of Xanthobacter strain Py2 was investigated. Cell suspensions prepared from cultures grown with propylene as the carbon source readily degraded epichlorohydrin. The ability to degrade epichlorohydrin correlated with the expression of enzymes involved in alkene and epoxide metabolism, since cell suspensions prepared from cultures grown with glucose or acetone, in which the enzymes of alkene and epoxide oxidation are not expressed, did not degrade epichlorohydrin. The alkene monooxygenase-specific inhibitor propyne had no effect on the degradation of epichlorohydrin, demonstrating that alkene monooxygenase is not involved in epichlorohydrin conversion. The interaction of epichlorohydrin and epibromohydrin with the epoxidase which catalyzes aliphatic epoxide conversions was established by showing that the epihalohydrins were specific and potent inhibitors of propylene oxide-dependent O 2 consumption by cell suspensions. The rates of degradation of epoxides in whole-cell suspensions decreased in the series propylene oxide > epifluorohydrin > epichlorohydrin > epibromohydrin. The pathway of epichlorohydrin degradation was investigated and found to proceed with stoichiometric dechlorination of epichlorohydrin. The first detectable product of epichlorohydrin degradation was chloroacetone. Chloroacetone was further degraded by the cell suspensions, and in the process, acetone was formed as a nonstoichiometric product. Acetone was further degraded by the cell suspensions with enzymes apparently induced by the accumulation of acetone. The metabolism of allyl chloride (3-chloropropylene) by propylene-grown cells was initiated by alkene monooxygenase and proceeded through epichlorohydrin, chloroacetone, and acetone as intermediate degradation products. These studies reveal a new pathway for halogenated epoxide degradation which involves halogenated and aliphatic ketones as well as other unidentified intermediates and which is unique from previously characterized hydrolytic degradative pathways.

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“…A produção seletiva do isômero "L" é essencial pois a forma isomérica "D" é tóxica para o organismo humano 3,6,7 . A produção de um alto excesso enantiomérico varia com a cepa (linhagem) usada do microorganismo 8,9 . O químico orgânico utiliza cepas comerciais deste microorganismo (no caso, fermento biológico de padaria) e como cada fabricante de fermento utiliza sua própria cepa, a qual tem características bioquímicas 2,3 e morfológicas próprias 10 , a reprodutibilidade Figura 1B.…”

Section: Introductionunclassified

Projeto e construção de um bioreator para síntese orgânica assimétrica catalisada por saccharomyces cerevisiae (fermento biológico de padaria)

Pereira¹

1997

Quím. Nova

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Recebido em 25/9/96; aceito em 2/4/97 PROJECT AND CONSTRUCTION OF A BIOREACTOR FOR REACTIONS CATALYZED BY BAKER'S YEAST (Saccharomyces cerevisiae). A model for the construction of a simple and cheap apparatus to be used as bioreactor for reactions catalyzed by baker's yeast (Saccharomyces cerevisiae) is described. The bioconversion and separation of cells from products and residual substrates are obtained at the same time. The reactions carried out in this type of reactor are faster than those catalyzed by immobilized cells. Yeast cells can be cultivated in this bioreactor operating with cell recycling at appropriated conditions using glucose and other nutrients.

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Synthesis of optically pure 1,2-epoxypropane by microbial asymmetric reduction of chloroacetone

Cited by 17 publications

References 24 publications

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

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

Characterization of a new pathway for epichlorohydrin degradation by whole cells of xanthobacter strain py2

Projeto e construção de um bioreator para síntese orgânica assimétrica catalisada por saccharomyces cerevisiae (fermento biológico de padaria)

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