Literature DB >> 23632017

Reactive intermediates in cytochrome p450 catalysis.

Courtney M Krest1, Elizabeth L Onderko, Timothy H Yosca, Julio C Calixto, Richard F Karp, Jovan Livada, Jonathan Rittle, Michael T Green.   

Abstract

Recently, we reported the spectroscopic and kinetic characterizations of cytochrome P450 compound I in CYP119A1, effectively closing the catalytic cycle of cytochrome P450-mediated hydroxylations. In this minireview, we focus on the developments that made this breakthrough possible. We examine the importance of enzyme purification in the quest for reactive intermediates and report the preparation of compound I in a second P450 (P450ST). In an effort to bring clarity to the field, we also examine the validity of controversial reports claiming the production of P450 compound I through the use of peroxynitrite and laser flash photolysis.

Entities:  

Keywords:  Cytochrome P450; Enzyme Catalysis; Enzyme Purification; Heme; P450 Compound I; Spectroscopy

Mesh:

Substances:

Year:  2013        PMID: 23632017      PMCID: PMC3682513          DOI: 10.1074/jbc.R113.473108

Source DB:  PubMed          Journal:  J Biol Chem        ISSN: 0021-9258            Impact factor:   5.157


  47 in total

1.  Cytochrome P450: the active oxidant and its spectrum.

Authors:  Jonathan Rittle; Jarod M Younker; Michael T Green
Journal:  Inorg Chem       Date:  2010-04-19       Impact factor: 5.165

2.  Cytochrome P450 compound I: capture, characterization, and C-H bond activation kinetics.

Authors:  Jonathan Rittle; Michael T Green
Journal:  Science       Date:  2010-11-12       Impact factor: 47.728

3.  C-H bond activation in heme proteins: the role of thiolate ligation in cytochrome P450.

Authors:  Michael T Green
Journal:  Curr Opin Chem Biol       Date:  2009-04-03       Impact factor: 8.822

4.  Aliphatic hydroxylation by highly purified liver microsomal cytochrome P-450. Evidence for a carbon radical intermediate.

Authors:  J T Groves; G A McClusky
Journal:  Biochem Biophys Res Commun       Date:  1978-03-15       Impact factor: 3.575

5.  Structure, electronic properties and catalytic behaviour of an activity-enhancing CYP102A1 (P450(BM3)) variant.

Authors:  Christopher J C Whitehouse; Wen Yang; Jake A Yorke; Henry G Tufton; Lydia C I Ogilvie; Stephen G Bell; Weihong Zhou; Mark Bartlam; Zihe Rao; Luet-Lok Wong
Journal:  Dalton Trans       Date:  2011-05-20       Impact factor: 4.390

6.  Photooxidation of cytochrome P450-BM3.

Authors:  Maraia E Ener; Young-Tae Lee; Jay R Winkler; Harry B Gray; Lionel Cheruzel
Journal:  Proc Natl Acad Sci U S A       Date:  2010-10-14       Impact factor: 11.205

Review 7.  Hydrocarbon hydroxylation by cytochrome P450 enzymes.

Authors:  Paul R Ortiz de Montellano
Journal:  Chem Rev       Date:  2010-02-10       Impact factor: 60.622

8.  Kinetics and activation parameters for oxidations of styrene by Compounds I from the cytochrome P450(BM-3) (CYP102A1) heme domain and from CYP119.

Authors:  Xinting Yuan; Qin Wang; John H Horner; Xin Sheng; Martin Newcomb
Journal:  Biochemistry       Date:  2009-09-29       Impact factor: 3.162

9.  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.

Authors:  Qin Wang; Xin Sheng; John H Horner; Martin Newcomb
Journal:  J Am Chem Soc       Date:  2009-08-05       Impact factor: 15.419

10.  Cytochrome P450 119 Compounds I Formed by Chemical Oxidation and Photooxidation Are the Same Species.

Authors:  Zhi Su; John H Horner; Martin Newcomb
Journal:  Chemistry       Date:  2012-10-29       Impact factor: 5.236

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  51 in total

Review 1.  Expanding P450 catalytic reaction space through evolution and engineering.

Authors:  John A McIntosh; Christopher C Farwell; Frances H Arnold
Journal:  Curr Opin Chem Biol       Date:  2014-03-20       Impact factor: 8.822

2.  Electronic State of the His/Tyr-Ligated Heme of BthA by Mössbauer and DFT Analysis.

Authors:  Andrew C Weitz; Saborni Biswas; Kim Rizzolo; Sean Elliott; Emile L Bominaar; Michael P Hendrich
Journal:  Inorg Chem       Date:  2020-06-30       Impact factor: 5.165

3.  Insights into an efficient light-driven hybrid P450 BM3 enzyme from crystallographic, spectroscopic and biochemical studies.

Authors:  Jessica Spradlin; Diana Lee; Sruthi Mahadevan; Mavish Mahomed; Lawrence Tang; Quan Lam; Alexander Colbert; Oliver S Shafaat; David Goodin; Marco Kloos; Mallory Kato; Lionel E Cheruzel
Journal:  Biochim Biophys Acta       Date:  2016-09-14

4.  Kinetic Modeling of Steady-State Situations in Cytochrome P450 Enzyme Reactions.

Authors:  F Peter Guengerich
Journal:  Drug Metab Dispos       Date:  2019-08-19       Impact factor: 3.922

Review 5.  Spectroscopic studies of the cytochrome P450 reaction mechanisms.

Authors:  Piotr J Mak; Ilia G Denisov
Journal:  Biochim Biophys Acta Proteins Proteom       Date:  2017-06-28       Impact factor: 3.036

Review 6.  Nitric oxide synthase enzymology in the 20 years after the Nobel Prize.

Authors:  Dennis J Stuehr; Mohammad Mahfuzul Haque
Journal:  Br J Pharmacol       Date:  2018-12-09       Impact factor: 8.739

Review 7.  Formation and Cleavage of C-C Bonds by Enzymatic Oxidation-Reduction Reactions.

Authors:  F Peter Guengerich; Francis K Yoshimoto
Journal:  Chem Rev       Date:  2018-06-22       Impact factor: 60.622

Review 8.  The diverse chemistry of cytochrome P450 17A1 (P450c17, CYP17A1).

Authors:  Francis K Yoshimoto; Richard J Auchus
Journal:  J Steroid Biochem Mol Biol       Date:  2014-12-04       Impact factor: 4.292

9.  Regio- and stereoselective hydroxylation of 10-undecenoic acid with a light-driven P450 BM3 biocatalyst yielding a valuable synthon for natural product synthesis.

Authors:  Mallory Kato; Daniel Nguyen; Melissa Gonzalez; Alejandro Cortez; Sarah E Mullen; Lionel E Cheruzel
Journal:  Bioorg Med Chem       Date:  2014-06-05       Impact factor: 3.641

10.  A Promiscuous Cytochrome P450 Hydroxylates Aliphatic and Aromatic C-H Bonds of Aromatic 2,5-Diketopiperazines.

Authors:  Guangde Jiang; Yi Zhang; Magan M Powell; Sarah M Hylton; Nicholas W Hiller; Rosemary Loria; Yousong Ding
Journal:  Chembiochem       Date:  2019-03-27       Impact factor: 3.164

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