Enantioconvergent bioconversion of p-chlorostyrene oxide to (R)-p-chlorophenyl-1,2-ethandiol by the bacterial epoxide hydrolase of Caulobacter crescentus.

The enantioselective hydrolysis of eight racemic styrene oxide derivatives has been investigated by using the recombinant cell containing epoxide hydrolase (EH) of Caulobacter crescentus. Some styrene oxide derivatives were hydrolyzed via enantioconvergent manner so that enantiopure diol products could be prepared with a 100% theoretical yield. The recombinant cell containing C. crescentus EH exhibited an ability to hydrolyze racemic p-chlorostyrene oxide the most enantioconvergently, thus affording the formation of the corresponding (R)-diol with enantiomeric excess (ee) as high as 95% and a 72% yield in preparative-scale (16.8 g/l) bioconversion.