Different enantioselectivity and regioselectivity of the cytosolic and microsomal epoxide hydrolase catalyzed hydrolysis of simple phenyl substituted epoxides

Article abstract of DOI:10.1016/S0040-4039(00)73156-X

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 attack at the benzylic carbon of 1-phenylpropene oxide.