Literature DB >> 19747698

Mechanistic aspects of CYP74 allene oxide synthases and related cytochrome P450 enzymes.

Alan R Brash1.   

Abstract

The existence of CYP5, CYP8A, and the CYP74 enzymes specialized for reaction with fatty acid peroxide substrates presents opportunities for a "different look" at the catalytic cycle of the cytochrome P450s. This review considers how the properties of the peroxide-metabolizing enzymes are distinctive, and how they tie in with those of the conventional monooxygenase enzymes. Some unusual reactions of each class have parallels in the other. As enzyme reactions and P450 structures emerge there will be possibilities for finding their special properties and edging this knowledge into the big picture.

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Year:  2009        PMID: 19747698      PMCID: PMC2783490          DOI: 10.1016/j.phytochem.2009.08.005

Source DB:  PubMed          Journal:  Phytochemistry        ISSN: 0031-9422            Impact factor:   4.072


  73 in total

1.  Allene oxide synthase from Arabidopsis thaliana (CYP74A1) exhibits dual specificity that is regulated by monomer-micelle association.

Authors:  Richard K Hughes; Eric J Belfield; Ruth Ashton; Shirley A Fairhurst; Cornelia Göbel; Michael Stumpe; Ivo Feussner; Rod Casey
Journal:  FEBS Lett       Date:  2006-07-05       Impact factor: 4.124

2.  New cyclopentenone fatty acids formed from linoleic and linolenic acids in potato.

Authors:  M Hamberg
Journal:  Lipids       Date:  2000-04       Impact factor: 1.880

3.  CYP74C3 and CYP74A1, plant cytochrome P450 enzymes whose activity is regulated by detergent micelle association, and proposed new rules for the classification of CYP74 enzymes.

Authors:  R K Hughes; E J Belfield; R Casey
Journal:  Biochem Soc Trans       Date:  2006-12       Impact factor: 5.407

4.  Identification of PpoA from Aspergillus nidulans as a fusion protein of a fatty acid heme dioxygenase/peroxidase and a cytochrome P450.

Authors:  Florian Brodhun; Cornelia Göbel; Ellen Hornung; Ivo Feussner
Journal:  J Biol Chem       Date:  2009-03-13       Impact factor: 5.157

5.  Isotope effect studies on the mechanism of the cytochrome P-450IIA1-catalyzed formation of delta 6-testosterone from testosterone.

Authors:  K R Korzekwa; W F Trager; K Nagata; A Parkinson; J R Gillette
Journal:  Drug Metab Dispos       Date:  1990 Nov-Dec       Impact factor: 3.922

6.  The major protein of guayule rubber particles is a cytochrome P450. Characterization based on cDNA cloning and spectroscopic analysis of the solubilized enzyme and its reaction products.

Authors:  Z Pan; F Durst; D Werck-Reichhart; H W Gardner; B Camara; K Cornish; R A Backhaus
Journal:  J Biol Chem       Date:  1995-04-14       Impact factor: 5.157

Review 7.  High-valent iron in chemical and biological oxidations.

Authors:  John T Groves
Journal:  J Inorg Biochem       Date:  2006-03-03       Impact factor: 4.155

Review 8.  The status of high-valent metal oxo complexes in the P450 cytochromes.

Authors:  Thomas M Makris; Konstanze von Koenig; Ilme Schlichting; Stephen G Sligar
Journal:  J Inorg Biochem       Date:  2006-02-28       Impact factor: 4.155

9.  Molecular cloning of an allene oxide synthase: a cytochrome P450 specialized for the metabolism of fatty acid hydroperoxides.

Authors:  W C Song; C D Funk; A R Brash
Journal:  Proc Natl Acad Sci U S A       Date:  1993-09-15       Impact factor: 11.205

Review 10.  Mechanisms of cytochrome P450 substrate oxidation: MiniReview.

Authors:  F Peter Guengerich
Journal:  J Biochem Mol Toxicol       Date:  2007       Impact factor: 3.642

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  32 in total

1.  Oxidation of C18 Hydroxy-Polyunsaturated Fatty Acids to Epoxide or Ketone by Catalase-Related Hemoproteins Activated with Iodosylbenzene.

Authors:  Tarvi Teder; William E Boeglin; Alan R Brash
Journal:  Lipids       Date:  2017-06-19       Impact factor: 1.880

Review 2.  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

3.  Cross-linking of dicyclotyrosine by the cytochrome P450 enzyme CYP121 from Mycobacterium tuberculosis proceeds through a catalytic shunt pathway.

Authors:  Kednerlin Dornevil; Ian Davis; Andrew J Fielding; James R Terrell; Li Ma; Aimin Liu
Journal:  J Biol Chem       Date:  2017-06-30       Impact factor: 5.157

4.  Cytochrome P450-type hydroxylation and epoxidation in a tyrosine-liganded hemoprotein, catalase-related allene oxide synthase.

Authors:  William E Boeglin; Alan R Brash
Journal:  J Biol Chem       Date:  2012-05-24       Impact factor: 5.157

Review 5.  Heme enzyme structure and function.

Authors:  Thomas L Poulos
Journal:  Chem Rev       Date:  2014-01-08       Impact factor: 60.622

6.  A Catalase-related Hemoprotein in Coral Is Specialized for Synthesis of Short-chain Aldehydes: DISCOVERY OF P450-TYPE HYDROPEROXIDE LYASE ACTIVITY IN A CATALASE.

Authors:  Tarvi Teder; Helike Lõhelaid; William E Boeglin; Wade M Calcutt; Alan R Brash; Nigulas Samel
Journal:  J Biol Chem       Date:  2015-06-22       Impact factor: 5.157

Review 7.  Oxygen Activation and Radical Transformations in Heme Proteins and Metalloporphyrins.

Authors:  Xiongyi Huang; John T Groves
Journal:  Chem Rev       Date:  2017-12-29       Impact factor: 60.622

8.  An ancient relative of cyclooxygenase in cyanobacteria is a linoleate 10S-dioxygenase that works in tandem with a catalase-related protein with specific 10S-hydroperoxide lyase activity.

Authors:  Alan R Brash; Narayan P Niraula; William E Boeglin; Zahra Mashhadi
Journal:  J Biol Chem       Date:  2014-03-21       Impact factor: 5.157

9.  Expression of fusion proteins of Aspergillus terreus reveals a novel allene oxide synthase.

Authors:  Inga Hoffmann; Fredrik Jernerén; Ernst H Oliw
Journal:  J Biol Chem       Date:  2013-03-11       Impact factor: 5.157

Review 10.  The Thr-His Connection on the Distal Heme of Catalase-Related Hemoproteins: A Hallmark of Reaction with Fatty Acid Hydroperoxides.

Authors:  Zahra Mashhadi; Marcia E Newcomer; Alan R Brash
Journal:  Chembiochem       Date:  2016-09-22       Impact factor: 3.164

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