Determination of the regiochemistry of insect epoxide hydrolase catalyzed epoxide hydration of juvenile hormone by 18O-labeling studies

Article abstract of DOI:10.1016/0040-4020(95)00678-2

The regiochemistry of Trichoplusia ni epoxide hydrolase catalyzed epoxide hydration of insect juvenile hormone (JH) III has been determined by GC/MS studies of ¹⁸O-label incorporation. Nucleophilic addition occurs at C10 of the C10,11 epoxide of JH III. The identification of isotopically labeled and unlabeled diol from the enzyme catalyzed hydration reaction in H₂¹⁸O implies that a covalently bound ester intermediate may be involved in the mechanism of the reaction.