The explosive-degrading cytochrome P450 XplA: Biochemistry, structural features and prospects for bioremediation

Biochimica et Biophysica Acta - Proteins and Proteomics

Volumn 1814, Issue 1, 2011, Pages 230-236

  Rylott, Elizabeth L ^a   Jackson, Rosamond G ^a   Sabbadin, Federico ^a   Seth Smith, Helena M B ^b   Edwards, James ^a   Chong, Chun Shiong ^a   Strand, Stuart E ^c   Grogan, Gideon ^a   Bruce, Neil C ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

^b WELLCOME TRUST SANGER INSTITUTE   (United Kingdom)

^c University of Washington   (United States)

Author keywords

Bioremediation; Cytochrome P450; Explosive; Phytoremediation; RDX; XplA; XplB

Indexed keywords

CYCLONITE; CYTOCHROME P450; CYTOCHROME P450 XPLA; CYTOCHROME P450 XPLB; HEME; OXYGEN; UNCLASSIFIED DRUG;

BIODEGRADATION; BIOREMEDIATION; CATABOLISM; ENZYME STRUCTURE; PRIORITY JOURNAL; REVIEW; SOIL POLLUTION; X RAY;

EID: 78649447000     PISSN: 15709639     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbapap.2010.07.004     Document Type: Article

References (45)

1. L.P. Wackett, M.J. Sadowsky, B. Martinez, and N. Shapir Biodegradation of atrazine and related s-triazine compounds: from enzymes to field studies Appl. Microbiol. Biotechnol. 58 2001 39 45
2. R. Lal, G. Pandey, P. Sharma, K. Kumari, S. Malhotra, R. Pandey, V. Raina, H.-P. Kohler, E. Holliger, C. Jackson, and J.G. Oakeshott Biochemistry of microbial degradation of hexachlorocyclohexane and prospects for bioremediation Microbiol. Mol. Biol. Rev. 74 2010 58 80
3. J.C. Lynch, K.F. Myers, J.M. Brannon, and J.J. Delfino Effects of pH and temperature on the aqueous solubility and dissolution rate of 2, 4, 6-trinitrotoluene (TNT), hexahydro-1, 3, 5-trinitro-1, 3, 5-triazine (RDX) and octahydro-1, 3, 5, 7-tetracine (HMX) J. Chem. Eng. Data 46 2001 1549 1555
4. United States General Accounting Office Department of Defense Operational Ranges More Reliable Cleanup Cost Estimates and a Proactive Approach to Identifying Contamination Are Needed (Report to Congressional Requesters) 2004 (http://www.dtic.mil/cgi-bin/GetTRDoc?AD=ADA435939&Location=U2&doc= GetTRDoc.pdf )
5. US Defense Science Board Task Force Unexploded Ordnance (UXO) Clearance, Active Range UXO Clearance, and Explosive Ordnance Disposal (EOD) Programs 1998 Office of the Undersecretary of Defense for Acquisition and Technology Washington, D.C (http://www.acq.osd.mil/dsb/reports/uxoandeod.pdf )
6. J. Clausen, J. Robb, D. Curry, and N. Korte A case study of contaminants on military ranges: Camp Edwards, Massachusetts, USA Environ. Pollut. 129 2004 13 21
7. L.J. Burdette, L.L. Cook, and R.S. Dyer Convulsant properties of cyclotrimethylenetrinitramine (RDX): spontaneous audiogenic, and bifunctional N- and O-glucosyltransferase involved in xenobiotic amygdaloid kindled seizure activity Toxicol. Appl. Pharmacol. 92 1988 436 444
8. Y. Kucukardali, H.V. Acar, S. Ozkan, S. Nalbant, Y. Yazgan, E.M. Atasoyu, O. Keskin, A. Naz, N. Akyatan, M. Gokben, and M. Danaci Accidental oral poisoning caused by RDX (cyclonite): a report of 5 cases J. Intensive Care Med. 18 2003 42 46
9. R.C. Woody, G.L. Kearns, M.A. Brewster, C.P. Turley, G.B. Sharp, and R.S. Lake The neurotoxicity of cyclotrimethylenetrinitramine (RDX) in a child: a clinical and pharmacokinetic evaluation J. Toxicol. Clin. Toxicol. 24 1986 305 319
10. C.E. French, S.J. Rosser, and N.C. Bruce Biotransformations of Explosives Biotechnol. Genet. Eng. Rev. 18 2001 171 217
11. S.J. Rosser, A. Basran, E. Travis, C.E. French, and N.C. Bruce Microbial transformations of explosives A.I. Laskin, J.W. Bennett, G.M. Gadd, Advances in Applied Microbiology 2001 Academic Press New York 1 35
12. N.G. McCormick, J.H. Cornell, and A.M. Kaplan Biodegradation of hexahydro-1, 3, 5-trinitro-1, 3, 5-triazine Appl. Environ. Microbiol. 42 1981 817 823
13. J. Hawari, A. Halasz, T. Sheremata, S. Beaudet, C. Groom, L. Paquet, C. Rhofir, G. Ampleman, and S. Thiboutot Characterization of metabolites during biodegradation of hexahydro-1, 3, 5-trinitro-1, 3, 5-triazine (RDX) with municipal anaerobic sludge Appl. Environ. Microbiol. 66 2000 2652 2657
14. F.H. Crocker, K.J. Indest, and H.L. Fredrickson Biodegradation of the cyclic nitramine explosives RDX, HMX, and CL-20 Appl. Microbiol. Biotechnol. 73 2006 274 290
15. N.V. Coleman, D.R. Nelson, and T. Duxbury Aerobic biodegradation of hexahydro-1, 3, 5-trinitro-1, 3, 5-triazine (RDX) as a nitrogen source by a Rhodococcus sp., strain DN22 Soil Biol. Biochem. 30 1998 1159 1167
16. H.M.B. Seth-Smith, S.J. Rosser, A. Basran, E.R. Travis, E.R. Dabbs, S. Nicklin, and N.C. Bruce Cloning, sequencing, and characterization of the hexahydro-1, 3, 5-trinitro-1, 3, 5-triazine degradation gene cluster from Rhodococcus rhodochrous Appl. Environ. Microbiol. 68 2002 4764 4771
17. A. Nejidat, L. Kafka, Y. Tekoah, and Z. Ronen Effect of organic and inorganic nitrogenous compounds on RDX degradation and cytochrome P450 expression in Rhodococcus strain YH1 Biodegradation 19 2008 313 320
18. K.T. Thompson, F.H. Crocker, and H.L. Fredrickson Mineralization of the cyclic nitramine explosive hexahydro-1,3,5-trinitro-1,3,5-triazine by Gordonia and Williamsia spp Appl. Environ. Microbiol. 71 2005 8265 8272
19. H.M.B. Seth-Smith, J. Edwards, S.J. Rosser, D.A. Rathbone, and N.C. Bruce The explosive degrading cytochrome P450 system is highly conserved between strains of Rhodococcus Appl. Environ. Microbiol. 74 2008 4550 4552
20. P.F. Andeer, D.A. Stahl, N.C. Bruce, and S.E. Strand Lateral transfer of genes for hexahydro-1, 3, 5-trinitro-1, 3, 5-triazine (RDX) degradation Appl. Environ. Microbiol. 75 2009 3258 3268
21. D. Fournier, A. Halasz, J. Spain, P. Fiurasek, and J. Hawari Determination of key metabolites during biodegradation of hexahydro-1, 3, 5-trinitro-1, 3, 5-triazine with Rhodococcus sp. strain DN22 Appl. Environ. Microbiol. 68 2002 166 172
22. J. Hawari, S. Beaudet, A. Halasz, S. Thiboutot, and G. Ampleman Biodegradation of explosives: biotransformation versus mineralization Appl. Microbiol. Biotechnol. 54 2000 605 618
23. D. Fournier, A. Halasz, J. Spain, R.J. Spanggord, J.C. Bottaro, and J. Hawari Biodegradation of the hexahydro-1,3,5-trinitro-1,3,5- triazine ring cleavage product 4-nitro-2,4-diazabutanal by Phanerochaete chrysosporium Appl. Environ. Microbiol. 70 2004 1123 1128
24. D. Fournier, S. Trott, J. Hawari, and J. Spain Metabolism of the aliphatic nitramine 4-nitro-2, 4-diazabutanal by Methylobacterium sp. Strain JS178 Appl. Environ. Microbiol. 71 2005 4199 4202
25. Y. Sagara, Y. Takata, T. Miyata, T. Hara, and T. Horiuchi Cloning and sequence analysis of adrenodoxin reductase cDNA from bovine adrenal cortex J. Biochem. 102 1987 1333 1336
26. M.E. Fuller, K. McClay, J. Hawari, L. Paquet, T.E. Malone, B.G. Fox, and R.F. Steffan Transformation of RDX and other energetic compounds by xenobiotic reductases XenA and XenB Appl. Microbiol. Biotechnol. 84 2009 535 544
27. E.L. Rylott, R.G. Jackson, J. Edwards, G.L. Womack, H.M.B. Seth-Smith, D.A. Rathbone, S.E. Strand, and N.C. Bruce An explosive-degrading cytochrome P450 activity and its targeted application for the phytoremediation of RDX Nat. Biotechnol. 24 2006 216 219
28. R.G. Jackson, E.L. Rylott, D. Fournier, J. Hawari, and N.C. Bruce Exploring the biochemical properties and remediation applications of the unusual explosive-degrading P450 system XplA/B Proc. Natl. Acad. Sci. USA 104 2007 16822 16827
29. A.W. Munro, H.M. Girvan, and K.J. McLean Variations on a (t)heme-novel mechanisms, redox partners and catalytic functions in the cytochrome P450 superfamily Nat. Prod. Rep. 24 2007 585 609
30. F. Sabbadin, R. Hyde, A. Robin, E.-M. Hilgarth, M. Delenne, S. Flitsch, N. Turner, G. Grogan, and N.C. Bruce LICRED: a versatile drop-in vector for rapid generation of redox self-sufficient cytochrome P450s Chembiochem 11 2010 987 994
31. J.A. Peterson, and D.M. Mock Metabolic control of cytochrome P 450cam Adv. Exp. Med. Biol. 58 1975 311 324
32. C.F. Melius Thermochemical modeling. I. Application to decomposition of energetic materials S.N. Bulusu, Chemistry and physics of energetic materials 1990 Kluwer Academic Publishers Dordrecht, The Netherlands 21 49
33. B. Bhushan, S. Trott, J.C. Spain, A. Halasz, L. Paquet, and J. Hawari Biotransformation of hexahydro-1, 3, 5-trinitro-1, 3, 5-triazine (RDX) by a rabbit liver Cytochrome P-450: insight into the mechanism of RDX biodegradation by Rhodococcus sp. strain DN22 Appl. Environ. Microbiol. 69 2003 1347 1351
34. F. Sabbadin, R.G. Jackson, K. Haider, G. Tampi, J.P. Turkenburg, S. Hart, N.C. Bruce, and G. Grogan The 1.5Å structure of XplA heme domain that catalyzes reductive biotransformation of Royal Demolition Explosive J. Biol. Chem. 284 2009 28467 28475
35. G.A. Roberts, G. Grogan, A. Greter, S.L. Flitsch, and N.J. Turner Identification of a New Class of Cytochrome P450 from a Rhodococcus sp J. Bacteriol. 184 2002 3898 3908
36. G.A. Roberts, A. Celik, D.J. Hunter, T.W. Ost, J.H. White, S.K. Chapman, N.J. Turner, and S.L. Flitsch A self-sufficient cytochrome P450 with a primary structural organization that includes a flavin domain and a [2Fe-2S] redox center J. Biol. Chem. 278 2003 48914 48920
37. D.J.B. Hunter, G.A. Roberts, T.W.B. Ost, J.H. White, S. Muller, N.J. Turner, S.L. Flitsch, and S.K. Chapman Analysis of the domain properties of the novel cytochrome P450RhF FEBS Lett. 579 2005 2215 2220
38. R. Neeli, H.M. Girvan, A. Lawrence, M.J. Warren, D. Leys, N.S. Scrutton, and A.W. Munro The dimeric form of flavocytochrome P450 BM3 is catalytically functional as a fatty acid hydroxylase FEBS Lett. 579 2005 5582 5588
39. T. Kitazume, D.C. Haines, R.W. Estabrook, B. Chen, and J.A. Peterson Obligatory intermolecular electron-transfer from FAD to FMN in dimeric P450BM-3 Biochemistry 46 2007 11892 11901
40. T.A. Lewis, D.A. Newcombe, and R.L. Crawford Bioremediation of soils contaminated with explosives J. Environ. Manage. 70 2004 291 307
41. E.L. Rylott, and N.C. Bruce Plants disarm soil: engineering plants for the phytoremediation of explosives Trends Biotechnol. 27 2009 73 81
42. C.L. Just, and J.L. Schnoor Phytophotolysis of hexahydro-1, 3, 5-trinitro-1, 3, 5-triazine (RDX) in leaves of reed canary grass Environ. Sci. Technol. 38 2004 290 295
43. E.P. Best, S.L. Sprecher, S.L. Larson, H.L. Fredrickson, and D.F. Bader Environmental behavior of explosives in groundwater from the Milan Army Ammunition Plant in aquatic and wetland plant treatments. Uptake and fate of TNT and RDX in plants Chemosphere 39 1999 2057 2072
44. L.E. Winfield, J.H. Rodgers Jr., and S.J. D'Surney The responses of selected terrestrial plants to short (< 12 days) and long term (2, 4 and 6 weeks) hexahydro-1, 3, 5-trinitro-1, 3, 5-triazine (RDX) exposure. Part I: growth and developmental effects Ecotoxicology 13 2004 335 347
45. M. Jackson, J.M. Green, R.L. Hash, D.C. Lindsten, and A.F. Tatyrek Nitramine (RDX-HMX) Wastewater Treatment at the Holston Army Ammunition Plant, Report ARLCD-77013 1978 U.S. Army Armament Research and Development Command Dover, NJ