PRODUCTION OF HIGHLY OPTICALLY-ACTIVE (R)-3-CHLORO-1,2-PROPANEDIOL USING A BACTERIUM ASSIMILATING THE (S)-ISOMER

A bacterium that assimilates (S)-3-chloro-1,2-propanediol [monochloroh ydrin (MCH)] was isolated from soil by enrichment culture. The bacteri um was identified as Pseudomonas sp. by taxonomic studies. The strain grew in a medium containing racemic MCH as a source of carbon and degr aded (S)-MCH stereoselectively, liberating chloride ions. The residual isomer was the (R)-form [99.5% enantiomeric excess (ee)], which was o btained 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 solutio n. The cell-free extracts of the cells had both dehalogenating and epo xide-opening activities, which converted various halohydrins to the co rresponding epoxides and epoxides to the corresponding diols, respecti vely.