Cyclopropyl fatty acids implicate a radical but not a cation as an intermediate in P450BM3-catalysed hydroxylations
- 1 January 2004
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Chemical Communications
- No. 5,p. 512-513
- https://doi.org/10.1039/b315911f
Abstract
Novel cyclopropyl containing fatty acids are good substrates for P450BM3 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.Keywords
This publication has 15 references indexed in Scilit:
- Carbon–carbon bond cleavage by cytochrome P450BioI(CYP107H1)Chemical Communications, 2003
- Products of Cytochrome P450BioI (CYP107H1)-Catalyzed Oxidation of Fatty AcidsOrganic Letters, 2003
- A Systematic Study of the Hydride Reduction of Cyclopropyl Ketones with Structurally Simplified Substrates. Highly Stereoselective Reductions ofTrans-Substituted Cyclopropyl Ketones via the Bisecteds-CisConformationThe Journal of Organic Chemistry, 2003
- Enzymatic Desaturation of Fatty Acids: Δ11 Desaturase Activity on Cyclopropane Acid ProbesThe Journal of Organic Chemistry, 2003
- Exploring new reactive species for cyclopropanationTetrahedron Letters, 1998
- Fatty acid monooxygenation by P450BM-3: Product identification and proposed mechanisms for the sequential hydroxylation reactionsArchives of Biochemistry and Biophysics, 1992
- A radical clock investigation of microsomal cytochrome P-450 hydroxylation of hydrocarbons. Rate of oxygen reboundJournal of the American Chemical Society, 1991
- Calibration of a new horologery of fast radical clocks. Ring-opening rates for ring- and .alpha.-alkyl-substituted cyclopropylcarbinyl radicals and for the bicyclo[2.1.0]pent-2-yl radicalJournal of the American Chemical Society, 1991
- Timing of the radical recombination step in cytochrome P-450 catalysis with ring-strained probesJournal of the American Chemical Society, 1987
- Trimethylsilyl tetrafluoroborate a convenient reagent for solvolysis reactionsTetrahedron Letters, 1984