A predictive pattern of computed barriers for C-h hydroxylation by compound I of cytochrome p450

Sam P de Visser; Devesh Kumar; Shimrit Cohen; Ronen Shacham; Sason Shaik

doi:10.1021/ja048528h

A predictive pattern of computed barriers for C-h hydroxylation by compound I of cytochrome p450

J Am Chem Soc. 2004 Jul 14;126(27):8362-3. doi: 10.1021/ja048528h.

Authors

Sam P de Visser¹, Devesh Kumar, Shimrit Cohen, Ronen Shacham, Sason Shaik

Affiliation

¹ Department of Chemistry and the Lise Meitner-Minerva Center for Computational Quantum Chemistry, The Hebrew University of Jerusalem, 91904 Jerusalem, Israel.

PMID: 15237977
DOI: 10.1021/ja048528h

Abstract

The communication presents DFT calculations of 10 different C-H hydroxylation barriers by the active species of the enzyme cytochrome P450. The work demonstrates the existence of an excellent barrier-bond energy correlation. The so-obtained equation of the straight line is demonstrated to be useful for predicting barriers of related C-H activation processes, as well as for assessing barrier heights within the protein environment. This facility is demonstrated be estimating the barrier of camphor hydroxylation by P450cam.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkanes / chemistry*
Alkanes / metabolism
Benzene Derivatives / chemistry
Benzene Derivatives / metabolism
Camphor 5-Monooxygenase / chemistry
Camphor 5-Monooxygenase / metabolism
Cytochrome P-450 Enzyme System / chemistry*
Cytochrome P-450 Enzyme System / metabolism
Ferric Compounds / chemistry
Ferric Compounds / metabolism
Hydrogen / chemistry
Hydrogen / metabolism
Hydroxylation
Iron Compounds / chemistry*
Iron Compounds / metabolism
Phenols / chemistry
Phenols / metabolism
Thermodynamics

Substances

Alkanes
Benzene Derivatives
Ferric Compounds
Iron Compounds
Phenols
ferric oxide
phenoxy radical
Hydrogen
Cytochrome P-450 Enzyme System
Camphor 5-Monooxygenase