Chemistry of extradiol aromatic ring cleavage: isolation of a stable dienol ring fission intermediate and stereochemistry of its enzymatic hydrolytic clevage

Abstract

The meta-ring fission intermediate on the phenylpropionate catabolic pathway exists as a stable trans-dienol; its breakdown by hydrolase enzyme MhpC proceeds with overall replacement of the succinyl group by a proton from water with retention of stereochemistry.