Enantioselective hydrolysis of racemic styrene oxide and its substituted derivatives using newly-isolated Sphingopyxis sp. exhibiting a novel epoxide hydrolase activity

Abstract

(S)-Styrene oxide, (S)-2-chlorostyrene oxide (CSO), (S)-3-CSO and (S)-4-CSO with 99.9%ee were obtained with a yield of 20.6, 39.3, 28.7 and 26.8% from 4mM corresponding racemic substrates using 10mg cells of a newly-isolated Sphingopyxis sp. at pH 8.0 and 25°C in 1ml 100mM Tris/HCl buffer after 420, 100, 120 and 55min, respectively. For racemic 2CSO, well-known for one of the racemates that is difficult to obtained in enantiomerically pure form, (S)-2-CSO with 99.9%ee, 39.3% yield (theoretical yield 50%) and enantiomeric ratio of 42.1 was obtained. The newly-isolated strain can thus be used as whole-cell biocatalyst in the production of various (S)-CSO with a chlorine group at different positions.