Enhanced <i>cis</i> - and enantioselective cyclopropanation of styrene catalysed by cytochrome P450BM3 using decoy molecules
Kazuto Suzuki, Yuma Shisaka, Joshua Kyle Stanfield, Yoshihito Watanabe, Osami Shoji
Abstract
We report the enhanced cis- and enantioselective cyclopropanation of styrene catalysed by cytochrome P450BM3 in the presence of dummy substrates, i.e. decoy molecules. With the aid of the decoy molecule R-Ibu-Phe, diastereoselectivity for the cis diastereomers reached 91%, and the enantiomeric ratio for the (1S,2R) isomer reached 94%. Molecular dynamics simulations underpin the experimental data, revealing the mechanism of how enantioselectivity is controlled by the addition of decoy molecules.
Topics & Concepts
CyclopropanationEnantioselective synthesisDecoyCytochromeStyreneChemistryMoleculeCombinatorial chemistryCatalysisOrganic chemistryBiochemistryEnzymeReceptorCopolymerPolymerCyclopropane Reaction MechanismsAsymmetric Hydrogenation and CatalysisSynthetic Organic Chemistry Methods