Substrate enantioselectivity in the rabbit liver microsomal epoxide hydrolase catalyzed hydrolysis of trans and cis 1-phenylpropene oxides. A comparison with styrene oxide

Article abstract of DOI:10.1016/S0957-4166(00)80222-0

A preferential consumption of the (1S,2S) enantiomer of (±)-trans-1-phenylpropene oxide (3) and of the (1R,2S) enantiomer of cis-1-phenylpropene oxide (5) is observed during the rabbit liver mEH catalyzed hydrolysis of these epoxides. This preference is, respectively, much lower and much higher than that found for the consumption of the (R) enantiomer in the hydrolysis of (±)-styrene oxide. These results are rationalized in terms of the K(M) and V(max) of the respective reactions.