title: Oxidation of 10-undecenoic acid by cytochrome P450(BM-3) and its Compound I transient.
abstract: Oxidations of 10-undecenoic acid by cytochrome P450(BM-3) and its Compound I transient were studied. The only product formed in Compound I oxidations was 10,11-epoxyundecanoic acid, whereas the enzyme under turnover conditions gave the epoxide and 9-hydroxy-10-undecenoic acid in a 10 : 90 ratio. Kinetic studies at 0 °C of oxidations by Compounds I formed by MCPBA oxidation and by a photo-oxidation pathway gave the same results, displaying saturation kinetics that yielded equilibrium binding constants and first-order oxidation rate constants that were experimentally indistinguishable. Oxidation of 10-undecenoic acid by Compound I from CYP119 generated by MCBPA oxidation also gave 10,11-epoxyundecanoic acid as the only product. CYP119 Compound I bound the substrate less strongly but reacted with a faster oxidation rate constant than P450(BM-3) Compound I. The kinetic parameters for oxidation of the substrate by P450(BM-3) under turnover conditions were similar to those of the Compound I transient even though the products differed.
authors: Department of Chemistry, University of Illinois at Chicago, 845 W. Taylor St., Chicago, IL 60607, USA. chenxh82@uic.edu
authors: Xiaohong
authors: X
authors: Chen
authors: Zhi
authors: Z
authors: Su
authors: John H
authors: JH
authors: Horner
authors: Martin
authors: M
authors: Newcomb
mesh_terms: D002412:Cations / Q000737:chemistry / Q000378:metabolism; D003577:Cytochrome P-450 Enzyme System / Q000737:chemistry / Q000378:metabolism*; D005229:Fatty Acids, Monounsaturated / Q000737:chemistry / Q000378:metabolism*; D005609:Free Radicals / Q000737:chemistry / Q000378:metabolism; D007700:Kinetics; D010084:Oxidation-Reduction; D011166:Porphyrins / Q000737:chemistry / Q000378:metabolism*; D014476:Undecylenic Acids
chemical_list: D002412:Cations; D005229:Fatty Acids, Monounsaturated; D005609:Free Radicals; D011166:Porphyrins; D014476:Undecylenic Acids; D003577:Cytochrome P-450 Enzyme System; C538763:undecylenic acid