ArticleJournal of the American Chemical Society2009
Quantitative production of compound I from a cytochrome P450 enzyme at low temperatures. Kinetics, activation parameters, and kinetic isotope effects for oxidation of benzyl alcohol.
Article in Journal of the American Chemical Society, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed, 62 citations in OpenAlex.
- Iridium-catalyzed α-selective deuteration of alcohols.Chemical science · 2022Article
- Cytochrome P450 119 Compounds I Formed by Chemical Oxidation and Photooxidation Are the Same Species.Chemistry (Weinheim an der Bergstrasse, Germany) · 2019Article
- Enhanced Activity and Substrate Specificity by Site-Directed Mutagenesis for the P450 119 Peroxygenase Catalyzed Sulfoxidation of Thioanisole.ChemistryOpen · 2019Article
- Oxygen Activation and Radical Transformations in Heme Proteins and Metalloporphyrins.Chemical reviews · 2018Review
- Thiol dioxygenase turnover yields benzothiazole products from 2-mercaptoaniline and OArchives of biochemistry and biophysics · 2017Article
- Beyond ferryl-mediated hydroxylation: 40 years of the rebound mechanism and C-H activation.Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry · 2017Review
- Reaction Intermediates and Molecular Mechanism of Peroxynitrite Activation by NO Synthases.Biophysical journal · 2016Article
- Reactive intermediates in cytochrome p450 catalysis.The Journal of biological chemistry · 2013Review
- Molecular probes of the mechanism of cytochrome P450. Oxygen traps a substrate radical intermediate.Archives of biochemistry and biophysics · 2011Article
- Photooxidation of cytochrome P450-BM3.Proceedings of the National Academy of Sciences of the United States of America · 2010Article
- Low temperature photo-oxidation of chloroperoxidase Compound II.Journal of inorganic biochemistry · 2010Article
- Mechanisms of peroxynitrite interactions with heme proteins.Inorganic chemistry · 2010Article
- Anilinic N-oxides support cytochrome P450-mediated N-dealkylation through hydrogen-atom transfer.Chemistry (Weinheim an der Bergstrasse, Germany) · 2010Article
- Probing 'spin-forbidden' oxygen-atom transfer: gas-phase reactions of chromium-porphyrin complexes.Journal of the American Chemical Society · 2010Article
- Oxidation of N-Nitrosoalkylamines by human cytochrome P450 2A6: sequential oxidation to aldehydes and carboxylic acids and analysis of reaction steps.The Journal of biological chemistry · 2010Article
- Kinetics and activation parameters for oxidations of styrene by Compounds I from the cytochrome P450(BM-3) (CYP102A1) heme domain and from CYP119.Biochemistry · 2009Article
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4 authors at 1 institution in 1 country.
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Abstract
Cytochrome P450 enzymes are commonly thought to oxidize substrates via an iron(IV)-oxo porphyrin radical cation transient termed Compound I, but kinetic studies of P450 Compounds I are essentially nonexistent. We report production of Compound I from cytochrome P450 119 (CYP119) in high conversion from the corresponding Compound II species at low temperatures in buffer mixtures containing 50% glycerol by photolysis with 365 nm light from a pulsed lamp. Compound I was studied as a reagent in oxidations of benzyl alcohol and its benzylic mono- and dideuterio isotopomers. Pseudo-first-order rate constants obtained at -50 degrees C with concentrations of substrates between 1.0 and 6.0 mM displayed saturation kinetics that gave binding constants for the substrate in the Compound I species (K(bind)) and first-order rate constants for the oxidation reactions (k(ox)). Representative results are K(bind) = 214 M(-1) and k(ox) = 0.48 s(-1) for oxidation of benzyl alcohol. For the dideuterated substrate C(6)H(5)CD(2)OH, kinetics were studied between -50 and -25 degrees C, and a van't Hoff plot for complexation and an Arrhenius plot for the oxidation reaction were constructed. The H/D kinetic isotope effects (KIEs) at -50 degrees C were resolved into a large primary KIE (P = 11.9) and a small, inverse secondary KIE (S = 0.96). Comparison of values extrapolated to 22 degrees C of both the rate constant for oxidation of C(6)H(5)CD(2)OH and the KIE for the nondeuterated and dideuterated substrates to values obtained previously in laser flash photolysis experiments suggested that tunneling could be a significant component of the total rate constant at -50 degrees C.
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