Literature DB >> 19692330

The 1.5-A structure of XplA-heme, an unusual cytochrome P450 heme domain that catalyzes reductive biotransformation of royal demolition explosive.

Federico Sabbadin1, Rosamond Jackson, Kamran Haider, Girish Tampi, Johan P Turkenburg, Sam Hart, Neil C Bruce, Gideon Grogan.   

Abstract

XplA is a cytochrome P450 of unique structural organization, consisting of a heme-domain that is C-terminally fused to its native flavodoxin redox partner. XplA, along with flavodoxin reductase XplB, has been shown to catalyze the breakdown of the nitramine explosive and pollutant hexahydro-1,3,5-trinitro-1,3,5-triazine (royal demolition explosive) by reductive denitration. The structure of the heme domain of XplA (XplA-heme) has been solved in two crystal forms: as a dimer in space group P2(1) to a resolution of 1.9 A and as a monomer in space group P2(1)2(1)2 to a resolution of 1.5 A, with the ligand imidazole bound at the heme iron. Although it shares the overall fold of cytochromes P450 of known structure, XplA-heme is unusual in that the kinked I-helix that traverses the distal face of the heme is broken by Met-394 and Ala-395 in place of the well conserved Asp/Glu plus Thr/Ser, important in oxidative P450s for the scission of the dioxygen bond prior to substrate oxygenation. The heme environment of XplA-heme is hydrophobic, featuring a cluster of three methionines above the heme, including Met-394. Imidazole was observed bound to the heme iron and is in close proximity to the side chain of Gln-438, which is situated over the distal face of the heme. Imidazole is also hydrogen-bonded to a water molecule that sits in place of the threonine side-chain hydroxyl exemplified by Thr-252 in Cyt-P450cam. Both Gln-438 --> Ala and Ala-395 --> Thr mutants of XplA-heme displayed markedly reduced activity compared with the wild type for royal demolition explosive degradation when combined with surrogate electron donors.

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Year:  2009        PMID: 19692330      PMCID: PMC2788895          DOI: 10.1074/jbc.M109.031559

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


  43 in total

1.  Comparison of the dynamics of substrate access channels in three cytochrome P450s reveals different opening mechanisms and a novel functional role for a buried arginine.

Authors:  Peter J Winn; Susanna K Lüdemann; Ralph Gauges; Valère Lounnas; Rebecca C Wade
Journal:  Proc Natl Acad Sci U S A       Date:  2002-04-16       Impact factor: 11.205

2.  Automated protein model building combined with iterative structure refinement.

Authors:  A Perrakis; R Morris; V S Lamzin
Journal:  Nat Struct Biol       Date:  1999-05

3.  Biotransformation of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) by a rabbit liver cytochrome P450: insight into the mechanism of RDX biodegradation by Rhodococcus sp. strain DN22.

Authors:  Bharat Bhushan; Sandra Trott; Jim C Spain; Annamaria Halasz; Louise Paquet; Jalal Hawari
Journal:  Appl Environ Microbiol       Date:  2003-03       Impact factor: 4.792

Review 4.  Common and uncommon cytochrome P450 reactions related to metabolism and chemical toxicity.

Authors:  F P Guengerich
Journal:  Chem Res Toxicol       Date:  2001-06       Impact factor: 3.739

5.  Ketoconazole-induced conformational changes in the active site of cytochrome P450eryF.

Authors:  J R Cupp-Vickery; C Garcia; A Hofacre; K McGee-Estrada
Journal:  J Mol Biol       Date:  2001-08-03       Impact factor: 5.469

6.  Atomic structure of Mycobacterium tuberculosis CYP121 to 1.06 A reveals novel features of cytochrome P450.

Authors:  David Leys; Christopher G Mowat; Kirsty J McLean; Alison Richmond; Stephen K Chapman; Malcolm D Walkinshaw; Andrew W Munro
Journal:  J Biol Chem       Date:  2002-11-14       Impact factor: 5.157

7.  Mutation effects of a conserved threonine (Thr243) of cytochrome P450nor on its structure and function.

Authors:  E Obayashi; H Shimizu; S Y Park; H Shoun; Y Shiro
Journal:  J Inorg Biochem       Date:  2000-11       Impact factor: 4.155

8.  An A245T mutation conveys on cytochrome P450eryF the ability to oxidize alternative substrates.

Authors:  H Xiang; R A Tschirret-Guth; P R Ortiz De Montellano
Journal:  J Biol Chem       Date:  2000-11-17       Impact factor: 5.157

9.  Cloning, sequencing, and characterization of the hexahydro-1,3,5-Trinitro-1,3,5-triazine degradation gene cluster from Rhodococcus rhodochrous.

Authors:  Helena M B Seth-Smith; Susan J Rosser; Amrik Basran; Emma R Travis; Eric R Dabbs; Steve Nicklin; Neil C Bruce
Journal:  Appl Environ Microbiol       Date:  2002-10       Impact factor: 4.792

10.  Substitutions at methionine 220 in the 14alpha-sterol demethylase (Cyp51A) of Aspergillus fumigatus are responsible for resistance in vitro to azole antifungal drugs.

Authors:  E Mellado; G Garcia-Effron; L Alcazar-Fuoli; M Cuenca-Estrella; J L Rodriguez-Tudela
Journal:  Antimicrob Agents Chemother       Date:  2004-07       Impact factor: 5.191

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  10 in total

Review 1.  Conformational plasticity and structure/function relationships in cytochromes P450.

Authors:  Thomas C Pochapsky; Sophia Kazanis; Marina Dang
Journal:  Antioxid Redox Signal       Date:  2010-10       Impact factor: 8.401

Review 2.  Unusual properties of the cytochrome P450 superfamily.

Authors:  David C Lamb; Michael R Waterman
Journal:  Philos Trans R Soc Lond B Biol Sci       Date:  2013-01-06       Impact factor: 6.237

3.  Analysis of the xplAB-containing gene cluster involved in the bacterial degradation of the explosive hexahydro-1,3,5-trinitro-1,3,5-triazine.

Authors:  Chun Shiong Chong; Dana Khdr Sabir; Astrid Lorenz; Cyril Bontemps; Peter Andeer; David A Stahl; Stuart E Strand; Elizabeth L Rylott; Neil C Bruce
Journal:  Appl Environ Microbiol       Date:  2014-08-15       Impact factor: 4.792

4.  Mechanism-Guided Design and Discovery of Efficient Cytochrome P450-Derived C-H Amination Biocatalysts.

Authors:  Viktoria Steck; Joshua N Kolev; Xinkun Ren; Rudi Fasan
Journal:  J Am Chem Soc       Date:  2020-06-01       Impact factor: 15.419

5.  Role of nitrogen limitation in transformation of RDX (hexahydro-1,3,5-trinitro-1,3,5-triazine) by Gordonia sp. strain KTR9.

Authors:  Karl J Indest; Dawn E Hancock; Carina M Jung; Jed O Eberly; William W Mohn; Lindsay D Eltis; Fiona H Crocker
Journal:  Appl Environ Microbiol       Date:  2012-12-28       Impact factor: 4.792

6.  Unusual spectroscopic and ligand binding properties of the cytochrome P450-flavodoxin fusion enzyme XplA.

Authors:  Soi H Bui; Kirsty J McLean; Myles R Cheesman; Justin M Bradley; Stephen E J Rigby; Colin W Levy; David Leys; Andrew W Munro
Journal:  J Biol Chem       Date:  2012-04-12       Impact factor: 5.157

7.  Functional characterization of pGKT2, a 182-kilobase plasmid containing the xplAB genes, which are involved in the degradation of hexahydro-1,3,5-trinitro-1,3,5-triazine by Gordonia sp. strain KTR9.

Authors:  Karl J Indest; Carina M Jung; Hao-Ping Chen; Dawn Hancock; Christine Florizone; Lindsay D Eltis; Fiona H Crocker
Journal:  Appl Environ Microbiol       Date:  2010-08-13       Impact factor: 4.792

8.  Genomic and transcriptomic studies of an RDX (hexahydro-1,3,5-trinitro-1,3,5-triazine)-degrading actinobacterium.

Authors:  Hao-Ping Chen; Song-Hua Zhu; Israël Casabon; Steven J Hallam; Fiona H Crocker; William W Mohn; Karl J Indest; Lindsay D Eltis
Journal:  Appl Environ Microbiol       Date:  2012-08-24       Impact factor: 4.792

Review 9.  Reductive Cytochrome P450 Reactions and Their Potential Role in Bioremediation.

Authors:  James B Y H Behrendorff
Journal:  Front Microbiol       Date:  2021-04-15       Impact factor: 5.640

10.  Expression in grasses of multiple transgenes for degradation of munitions compounds on live-fire training ranges.

Authors:  Long Zhang; Ryan Routsong; Quyen Nguyen; Elizabeth L Rylott; Neil C Bruce; Stuart E Strand
Journal:  Plant Biotechnol J       Date:  2016-12-29       Impact factor: 9.803

  10 in total

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