Preparation of (S)-2,3-dichloro-1-propanol byPseudomonas sp. and its use in the synthesis of (R)-epichlorohydrin

Kasai, Naoya; Tsujimura, Kazuya; Unoura, Kinya; Suzuki, Toshio

doi:10.1007/bf01569739

Cited by 37 publications

(28 citation statements)

References 16 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…in aqueous phase with a substrate concentration for 10.4 mM and the volumetric productivity is only 2.9 g (R)-DCP L −1 h −1 . Kasai et al (1992b) also reported the bio-resolution of (R,S)-DCP using HHDH from Pseudomonas sp. OS-K-29 in aqueous single-phase system with a substrate concentration for 22.1 mM and the volumetric productivity is only 0.004 g (S)-DCP L −1 h −1 .…”

Section: Bio-resolution Of Dcp In a Mechanically Stirred Reactormentioning

confidence: 95%

Enhancement of (S)-2,3-dichloro-1-propanol production by recombinant whole-cell biocatalyst in n-heptane–aqueous biphasic system

Zou

Zheng

et al. 2014

Journal of Biotechnology

View full text Add to dashboard Cite

Section: Bio-resolution Of Dcp In a Mechanically Stirred Reactormentioning

confidence: 95%

Enhancement of (S)-2,3-dichloro-1-propanol production by recombinant whole-cell biocatalyst in n-heptane–aqueous biphasic system

Zou

Zheng

et al. 2014

Journal of Biotechnology

View full text Add to dashboard Cite

“…(OS-K-29; Scheme 90). [213] The enantiomer (R)-230 could be obtained by degradation of (S)-230 with Alcaligenes sp. (DS-K-S38).…”

Section: Microbial Methods For Racemate Resolutionmentioning

confidence: 99%

Industrial Methods for the Production of Optically Active Intermediates

Breuer¹,

Ditrich²,

Habicher³

et al. 2004

Angew Chem Int Ed

1,316

625

View full text Add to dashboard Cite

Enantiomerically pure amino acids, amino alcohols, amines, alcohols, and epoxides play an increasingly important role as intermediates in the pharmaceutical industry and agrochemistry, where both a high degree of purity and large quantities of the compounds are required. The chemical industry has primarily relied upon established chemical methods for the synthesis of these intermediates, but is now turning more and more to enzymatic and biotechnological fermentation processes. For the industrial implementation of many transformations alternative methods are available. The advantages of the individual methods will be discussed herein and exemplified by syntheses of relevant compounds.

show abstract

“…Butylene chlorohydrin was prepared from butylene oxide by the addition of HC1 (Markownikoff 1870). (R)-and (S)-MCH were prepared from (R)-and (S)-epichlorohydrin (Kasai et al 1990(Kasai et al , 1992a, respectively, by hydration (Fourneau and Marquis 1926).…”

Section: Methodsmentioning

confidence: 99%

Production of highly optically active (R)-3-chloro-1,2-propanediol using a bacterium assimilating the (S)-isomer

Suzuki

Kasai

Yamamoto

et al. 1993

Appl Microbiol Biotechnol

Self Cite

View full text Add to dashboard Cite

A bacterium that assimilates (S)-3-chloro-1,2-propanediol [monochlorohydrin (MCH)] was isolated from soil by enrichment culture. The bacterium was identified as Pseudomonas sp. by taxonomic studies. The strain grew in a medium c~ontaining racemic MCH as a source of carbon and degraded (S)-MCH stereoseIectively, liberating chloride ions. The residual isomer was the (R)-form [99.5% enantiomeric excess (ee)], which was obtained from the racemate in a final yield of 36% by using this strain. Subsequently, highly optically active (R)-glycidol (GLD) (99.3% e e ) w a s prepared from the (R)-MCH obtained by reaction in alkaline solution. The cell-free extracts of the cells had both dehalogenating and epoxide-opening activities, which converted various halohydrins to the corresponding epoxides and epoxides to the corresponding diols, respectively.

show abstract

Preparation of (S)-2,3-dichloro-1-propanol byPseudomonas sp. and its use in the synthesis of (R)-epichlorohydrin

Cited by 37 publications

References 16 publications

Enhancement of (S)-2,3-dichloro-1-propanol production by recombinant whole-cell biocatalyst in n-heptane–aqueous biphasic system

Enhancement of (S)-2,3-dichloro-1-propanol production by recombinant whole-cell biocatalyst in n-heptane–aqueous biphasic system

Industrial Methods for the Production of Optically Active Intermediates

Production of highly optically active (R)-3-chloro-1,2-propanediol using a bacterium assimilating the (S)-isomer

Contact Info

Product

Resources

About