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*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

115 Scopus citations

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 pages5
JournalAngewandte Chemie - International Edition
Volume41
Issue number11
DOIs
StatePublished - 3 Jun 2002

Keywords

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

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