Angewandte Chemie International Edition · 1999 · 50 citations · 0 references
Life SciencesBiochemistryPharmacologyEnzyme MechanismMetabolismSteroid BiochemistryCytochrome P450 EnzymesCytochrome P450-mediated MetabolismReactive Metabolite FormationSteroid BiosynthesisSteroid MetabolismSteroidogenic EnzymesCytochrome P450 CatalysisCytochrome P450 PathwaysCytochrome P450 Reaction MechanismsCytochrome P450-mediated Steroid MetabolismCytochrome P450-mediated Terpenoid OxidationDealkylation ReactionsSteroid Side-chain CleavageSyn Elimination Geometry
In contrast to the stepwise oxidative dealkylation of steroids [Eq. (1)], (+)-marmesin (1) is directly converted by the psoralen synthase (a cytochrome P450) into the phototoxic furanocoumarin psoralen (2) and acetone. The dealkylation proceeds as a syn elimination.