Cyclopropyl fatty acids implicate a radical but not a cation as an intermediate in P450BM3-catalysed hydroxylations

Max J Cryle; Julia M U Stuthe; Paul R Ortiz de Montellano; James J De Voss

doi:10.1039/b315911f

Cyclopropyl fatty acids implicate a radical but not a cation as an intermediate in P450BM3-catalysed hydroxylations

Chem Commun (Camb). 2004 Mar 7:(5):512-3. doi: 10.1039/b315911f. Epub 2004 Jan 27.

Authors

Max J Cryle¹, Julia M U Stuthe, Paul R Ortiz de Montellano, James J De Voss

Affiliation

¹ Department of Chemistry, University of Queensland, St. Lucia, Brisbane, Australia 4072.

PMID: 14973583
DOI: 10.1039/b315911f

Abstract

Novel cyclopropyl containing fatty acids are good substrates for P450(BM3) catalysed hydroxylation and analysis of their oxidation products indicates the presence of a radical intermediate (maximum rebound rate 2.6 x 10(10) s(-1)) and the absence of any cationic intermediate.

Publication types

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

MeSH terms

Bacterial Proteins / metabolism*
Cations / chemistry
Cytochrome P-450 Enzyme System / metabolism*
Fatty Acids / chemistry
Fatty Acids / metabolism*
Gas Chromatography-Mass Spectrometry
Hydroxylation
Magnetic Resonance Spectroscopy
Mixed Function Oxygenases / metabolism*
Molecular Conformation
NADPH-Ferrihemoprotein Reductase
Oxidation-Reduction

Substances

Bacterial Proteins
Cations
Fatty Acids
Cytochrome P-450 Enzyme System
Mixed Function Oxygenases
NADPH-Ferrihemoprotein Reductase
flavocytochrome P450 BM3 monoxygenases