Hydrogen bonding modulates the selectivity of enzymatic oxidation by P450: Chameleon oxidant behavior by compound I

Samuël P. De Visser, François Ogliaro, Pankaz K. Sharma, Sason Shaik

    Research output: Contribution to journalArticlepeer-review

    Abstract

    Changes of two orders of magnitude or more in the epoxidation to hydroxylation ratio of propene by the iron-oxo species 1, the primary active species of cytochrome P450 (see scheme) occur when the molecular species is subject to NH ··· S hydrogen bonding and electronic polarization as in the protein pocket.
    Original languageEnglish
    Pages (from-to)1947-1951
    Number of pages4
    JournalAngewandte Chemie - International Edition
    Volume41
    Issue number11
    DOIs
    Publication statusPublished - 3 Jun 2002

    Keywords

    • Density functional calculations
    • Enzyme catalysis
    • Epoxidation
    • Hydroxylation
    • Solvent effects

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