DIFFERENT ENANTIOSELECTIVITY AND REGIOSELECTIVITY OF THE CYTOSOLIC AND MICROSOMAL EPOXIDE HYDROLASE CATALYZED-HYDROLYSIS OF SIMPLE PHENYL-SUBSTITUTED EPOXIDES

The cytosolic (cEH) and the microsomal epoxide hydrolase (mEH) hydrolyse styrene oxide and trans-1-phenylpropene oxide with different enantioselectivity and regioselectivity. While mEH always leads to a regiospecific and enantioselective opening at the non-benzylic oxirane carbon, cEH gives a non-regioselective and non-enantioselective attack to styrene oxide and a regiospecific and non-enantioselective snack at the benzylic carbon of 1-phenylpropene oxide.