Production of highly optically active (R)-3-chloro-1,2-propanediol using a bacterium assimilating the (S)-isomer |
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Authors: | Toshio Suzuki Naoya Kasai Ryoichi Yamamoto Noshi Minamiura |
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Institution: | (1) Research Laboratories of DAISO Co., Ltd., 9 Otakasu-cho, Amagasaki, 660 Hyogo, Japan;(2) Faculty of Science, Osaka City University, 3-3-138 Sugimoto, Sumiyoshi-ku, 558 Osaka, Japan |
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Abstract: | 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 containing racemic MCH as a source of carbon and degraded (S)-MCH stereoselectively, 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% ee) was 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.
Correspondence to: T. Suzuki |
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