Biodegradation of the Hexahydro-1,3,5-Trinitro-1,3,5-Triazine Ring Cleavage Product 4-Nitro-2,4-Diazabutanal by Phanerochaete chrysosporium

Applied and Environmental Microbiology

Volumn 70, Issue 2, 2004, Pages 1123-1128

  Fournier, Diane ^a   Halasz, Annamaria ^a   Spain, Jim ^b   Spanggord, Ronald J ^c   Bottaro, Jeffrey C ^c   Hawari, Jalal ^a  

^a NATIONAL RESEARCH COUNCIL CANADA   (Canada)

^b AIR FORCE RESEARCH LABORATORY   (United States)

^c SRI INTERNATIONAL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIA; CELL CULTURE; DEGRADATION; ENZYMES; FUNGI; ORGANIC COMPOUNDS; SOILS;

AMMUNITION PLANTS; BIOREMEDATION; INCUBATION;

BIODEGRADATION;

4 NITRO 2,4 DIAZABUTANAL; AZOCINE DERIVATIVE; BUTYRALDEHYDE; CARBON DIOXIDE; CYCLONITE; HEXAHYDRO 1 NITROSO 3,5 DINITRO 1,3,5 TRIAZINE; LIGNIN PEROXIDASE; MANGANESE PEROXIDASE; NITROGEN DERIVATIVE; NITROUS OXIDE; OCTAHYDRO 1,3,5,7 TETRANITRO 1,3,5,7 TETRAZOCINE; TRIAZINE DERIVATIVE; UNCLASSIFIED DRUG;

MICROBIOLOGY;

ARTICLE; BACTERIAL STRAIN; BIODEGRADABILITY; BIOREMEDIATION; BIOTECHNOLOGY; CULTURE MEDIUM; DENITRIFICATION; FIREARM; LIQUID CULTURE; MICROBIAL DEGRADATION; MINERALIZATION; NONHUMAN; PHANEROCHAETE; SOIL ANALYSIS; SOIL POLLUTANT; SOIL POLLUTION; STOICHIOMETRY;

ALDEHYDES; AZA COMPOUNDS; BIODEGRADATION, ENVIRONMENTAL; CULTURE MEDIA; INDUSTRIAL WASTE; PHANEROCHAETE; SOIL; SOIL POLLUTANTS; TRIAZINES;

BACTERIA (MICROORGANISMS); CHRYSOSPORIUM; FUNGI; PHANEROCHAETE; PHANEROCHAETE CHRYSOSPORIUM; RHODOCOCCUS; RHODOCOCCUS SP.;

EID: 2342581418     PISSN: 00992240     EISSN: None     Source Type: Journal    
DOI: 10.1128/AEM.70.2.1123-1128.2004     Document Type: Article

References (38)

1. 14C-labelled hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX), 2,4,6-trinitrotoluene (TNT), nitrocellulose (NC) and glycidylazide polymer (GAP) for use in assessing the biodegradation potential of these energetic compounds. J. Label. Compd. Radiopharm. 36:559-577.
2. Balakrishnan, V., A. Halasz, and J. Hawari. 2003. Alkaline hydrolysis of the cyclic nitramine explosives RDX, HMX, and CL-20: new insights into degradation pathways obtained by the observation of novel intermediates. Environ. Sci. Technol. 37:1838-1843.
3. Bayman, P., S. D. Ritchey, and J. W. Bennett. 1995. Fungal interactions with the explosive RDX (hexahydro-1,3,5-trinitro-1,3,5-triazine). J. Ind. Microbiol. 15:418-423.
4. Beller, H. R., and K. Tiemeier. 2002. Use of liquid chromatography/ tandem mass spectrometry to detect distinctive indicators of in situ RDX transformation in contaminated groundwater. Environ. Sci. Technol. 36:2060-2066.
5. Bhushan, B., A. Halasz, J. Spain, S. Thiboutot, G. Ampleman, and J. Hawari. 2002. Biotransformation of hexahydro-1,3,5-trinitro-1,3,5-triazine catalyzed by a NAD(P)H: nitrate oxidoreductase from Aspergillus niger. Environ. Sci. Technol. 36:3104-3108.
6. Bhushan, B., S. Trott, J. C. Spain, A. Halasz, L. Paquet, and J. Hawari. 2003. 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. Appl. Environ. Microbiol. 69:1347-1351.
7. Binks, P. R., S. Nicklin, and N. C. Bruce. 1995. Degradation of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) by Stenotrophomonas maltophilia PB1. Appl. Environ. Microbiol. 61:1318-1322.
8. Capdevila, C., S. Moukha, M. Ghyczy, J. Theilleux, B. Gelie, M. Delattre, G. Corrieu, and M. Asther. 1990. Characterization of peroxidase secretion and subcellular organization of Phanerochaete chrysosporium INA-12 in the presence of various soybean phospholipid fractions. Appl. Environ. Microbiol. 56:3811-3816.
9. Coleman, N. V., D. R. Nelson, and T. Duxbury. 1998. Aerobic degradation of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) as a nitrogen source by a Rhodococcus sp., strain DN22. Soil Biol. Biochem. 30:1159-1167.
10. Coleman, N. V., J. C. Spain, and T. Duxbury. 2002. Evidence that RDX biodegradation by Rhodococcus strain DN22 is plasmid-borne and involves a cytochrome p-450. J. Appl. Microbiol. 93:463-472.
11. Fernando, T., and S. D. Aust. 1991. Biodegradation of municipal waste, TNT (2,4,6-trinitrotoluene) and RDX (hexahydro-1,3,5-trinitro-1,3,5-triazine) by Phanerochaete chrysosporium, p. 214-231. In D. W. Tedder and F. G. Pohland (ed.), Emerging technologies in hazardous waste management. American Chemical Society, Washington, D.C.
12. Fournier, D., A. Halasz, J. C. Spain, P. Fiurasek, and J. Hawari. 2002. Determination of key metabolites during biodegradation of hexahydro-1,3,5-trinitro-1,3,5-triazine with Rhodococcus sp. strain DN22. Appl. Environ. Microbiol, 68:166-172.
13. Haas, R., I. Schreiber, E. von Löw, and G. Stork. 1990. Conception for the investigation of contaminated munitions plants. 2. Investigation of former RDX-plants and filling stations. Fresenius' J. Anal. Chem. 338:41-45.
14. Halasz, A., J. Spain, L. Paquet, C. Beaulieu, and J. Hawari. 2002. Insights into the formation and degradation mechanisms of methylenedinitramine during the incubation of RDX with anaerobic sludge. Environ. Sci. Technol. 36:633-638.
15. Hawari, J. 2000. Biodegradation of RDX and HMX: from basic research to field application, p. 277-310. In J. C. Spain, J. B. Hughes, and H,-J, Knackmuss (ed.), Biodegradation of nitroaromatic compounds and explosives. CRC Press, Boca Raton, Fla.
16. Hawari, J., A. Halasz, C. Groom, S. Deschamps, L. Paquet, C. Beaulieu, and A. Corriveau. 2002. Photodegradation of RDX in aqueous solution: a mechanistic probe for biodegradation with Rhodococcus sp. Environ. Sci. Technol. 36:5117-5123.
17. Hawari, J., A. Halasz, S. Beaudet, L. Paquet, G. Ampleman, and S. Thiboutot. 2001. Biotransformation routes of octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine by municipal anaerobic sludge. Environ. Sci. Technol. 35:70-75.
18. Hofrichter, M., K. Scheibner, I. Schneegall, and W. Fritsche. 1998. Enzymatic combustion of aromatic and aliphatic compounds by manganese peroxidase from Nematoloma frowardii. Appl. Environ. Microbiol. 64:399-404.
19. Jerger, D. E., and P. Woodhull. 2000. Applications and costs for biological treatment of explosives-contaminated soils in the US, p. 395-423. In J. C. Spain, J. B. Hughes, and H.-J. Knackmuss (ed.), Biodegradation of nitroaromatic compounds and explosives. CRC Press, Boca Raton, Fla.
20. Jones, A. M., C. W. Greer, G. Ampleman, S. Thiboutot, J. Lavigne, and J. Hawari. 1995. Biodegradability of selected highly energetic pollutants under aerobic conditions, p. 251-257. In R. E. Hinchee, D. B. Anderson, and R. E. Hoeppel (ed.), Bioremediation of recalcitrant organics. Battelle Press, Columbus, Ohio.
21. Kirk, T. K., and R. L. Farrell. 1987. Enzymatic "combustion": the microbial degradation of lignin. Annu. Rev. Microbiol. 41:465-505.
22. Kitts, C. L., D. P. Cunningham, and P. J. Unkefer. 1994. Isolation of three hexahydro-1,3,5-trinitro-1,3,5-triazine-degrading species of the family Enterobacteriaceae from nitramine explosive-contaminated soil. Appl. Environ. Microbiol. 60:4608-4711.
23. McCormick, N. G., J. H. Cornell, and A. M. Kaplan. 1981. Biodegradation of hexahydro-1,3,5-trinitro-1,3,5-triazine. Appl. Environ. Microbiol. 42:817-823.
24. Myler, C. A., and W. Sisk. 1991. Bioremediation of explosives contaminated soils (scientific questions/engineering realities), p. 137-146. In G. S. Sayler, R. Fox, and J. W. Blackburn (ed.), Environmental bio/technology for waste treatment. Plenum Press, New York, N.Y.
25. Oh, B.-T., C. L. Just, and P. J. J. Alvarez. 2001. Hexahydro-1,3,5-trinitro-1,3,5-triazine mineralization by zerovalent iron and mixed anaerobic cultures. Environ. Sci. Technol. 35:4341-4346.
26. Pennington, J. C., and J. M. Brannon. 2002. Environmental fate of explosives. Thermochim. Acta 384:163-172.
27. Robidoux, P. Y., J. Hawari, S. Thiboutot, G. Ampleman, and G. I. Sunahara. 2001. Chronic toxicity of octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX) in soil determined using the earthworm (Eisenia andrei) reproduction test. Environ. Pollut. 111:283-292.
28. Sauer, C. W., and R. P. Follett. 1955. Nitramines. I. Methylenedinitramine. J. Am. Chem. Soc. 77:2560-2561.
29. Seth-Smith, H. M. B., S. J. Rosser, A. Basran, E. R. Travis, E. R. Dabbs, S. Nicklin, and N. C. Bruce. 2002. Cloning, sequencing, and characterization of the hexahydro-1,3,5-trinitro-1,3,5-triazine degradation gene cluster from Rhodococcus rhodochrous. Appl. Environ. Microbiol. 68:4764-4771.
30. Sheremata, T. W., and J. Hawari. 2000. Mineralization of RDX by the white rot fungus Phanerochaete chrysosporium to carbon dioxide and nitrous oxide. Environ. Sci. Technol. 34:3384-3388.
31. Stahl, J. D., B. Van Aken, M. D. Cameron, and S. D. Aust. 2001. Hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) biodegradation in liquid and solid-state matrices by Phanerochaete chrysosporium. Bioremediation J. 5:13-25.
32. Sunahara, G. I., S. Dodard, M. Sarrazin, L. Paquet, G. Ampleman, S. Thiboutot, J. Hawari, and A. Y. Renoux. 1998. Development of a soil extraction procedure for ecotoxicity characterization of energetic compounds. Ecotoxicol. Environ. Safety 39:185-194.
33. Talmage, S. S., D. M. Opresko, C. J. Maxwel, C. J. E. Welsh, F. M. Cretella, P. H. Reno, and F. B. Daniel. 1999. Nitroaromatic munition compounds: environmental effects and screening values. Rev. Environ. Contam. Toxicol. 161:1-156.
34. U.S. Environmental Protection Agency. 1997. Method 8330 SW-846, update III, part 4. 1 (B), Nitroaromatics and nitramines by high performance liquid chromatography (HPLC). Office of Solid Waste, Washington, D.C.
35. Young, D. M., P. J. Unkefer, and K. L. Ogden. 1997. Biotransformation of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) by a prospective consortium and its most effective isolate, Serratia marcescens. Biotechnol. Bioeng. 53:515-522.
36. Zhao, J.-S., A. Halasz, L. Paquet, C. Beaulieu, and J. Hawari. 2002. Biodegradation of hexahydro-1,3,5-trinitro-1,3,5-triazine and its mononitroso derivative hexahydro-1-nitroso-3,5-dinitro-1,3,5-triazine by Klebsiella pneumoniae strain SCZ-I isolated from an anaerobic sludge. Appl. Environ. Microbiol. 68:5336-5341.
37. Zhao, J.-S., L. Paquet, A. Halasz, and J. Hawari. 2003. Metabolism of hexahydro-1,3,5-trinitro-1,3,5-triazine through initial reduction to hexahydro-1-nitroso-3,5-dinitro-1,3,5-triazine followed by denitration in Clostridium bifermentans HAW-1. Appl. Microbiol. Biotechnol. 63:187-193.
38. Zhao, J.-S., J. Spain, and J. Hawari. 2003. Phylogenetic and metabolic diversity of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX)-transforming bacteria in strictly anaerobic mixed cultures enriched on RDX as nitrogen source. FEMS Microbiol. Ecol. 46:189-196.