Methane monooxygenase biotransformations: Highly stereoselective hydroxylation of 3-methylcyclohexene by methane monooxygenase: Steric and electronic effects on product distribution

Cell extracts containing soluble methane monooxygenase from Methylococcus capsulatus, Methylosinus sporium and Methylosinus trichosporium converted 3-methylcyclohexene to predominantly cis-4-methylcyclohex-2-enol, contrary to an earlier suggestion of rearrangement products. In the case of M. capsulatus extracts, this comprised 90% of the total products. The product mixture was consistent with predictions based on chemical reactivity of the substrate, steric effects in the substrate and products and enzymic constraints operating in concert.