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

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Cyclopropyl fatty acids implicate a radical but not a cation as an intermediate in P450_BM3-catalysed hydroxylations†

Max J. Cryle,^a Julia M. U. Stuthe,^a Paul R. Ortiz de Montellano^b and James J. De Voss*^a

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* Corresponding authors

^a Department of Chemistry, University of Queensland, St. Lucia, Brisbane, Australia 4072
E-mail: j.devoss@uq.edu.au
Fax: 61 7 3365 4299
Tel: 61 7 3365 3825

^b Department of Pharmaceutical Chemistry, University of California, San Francisco, CA, USA 94143-2280
E-mail: ortiz@cgl.ucsf.edu
Fax: 415 502-4728
Tel: 415 476-2903

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 × 10¹⁰ s⁻¹) and the absence of any cationic intermediate.

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Supplementary files

Cationic rearrangement of 3, spectra of 3, 5, 7, 11–12, plus GCMS conditions for analysis of 1–5, 7–12 DOC (132K)

Article information

DOI: https://doi.org/10.1039/B315911F
Article type: Communication
Submitted: 05 Dec 2003
Accepted: 22 Dec 2003
First published: 27 Jan 2004

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Chem. Commun., 2004, 512-513

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Cyclopropyl fatty acids implicate a radical but not a cation as an intermediate in P450_BM3-catalysed hydroxylations

M. J. Cryle, J. M. U. Stuthe, P. R. Ortiz de Montellano and J. J. De Voss, Chem. Commun., 2004, 512 DOI: 10.1039/B315911F

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