Compound-specific isotope analysis of RDX and stable isotope fractionation during aerobic and anaerobic biodegradation

Environmental Science and Technology

Volumn 42, Issue 21, 2008, Pages 7772-7777

  Bernstein, Anat ^a   Ronen, Zeev ^a   Adar, Eilon ^a   Nativ, Ronit ^b   Lowag, Harald ^c   Stichler, Willibald ^c   Meckenstock, Rainer U ^c  

^a BEN GURION UNIVERSITY OF THE NEGEV   (Israel)

^b HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^c INSTITUTE OF EPIDEMIOLOGY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BATCH CELL CULTURE; BIOCHEMISTRY; CHROMATOGRAPHIC ANALYSIS; CONTAMINATION; DEGRADATION; ISOTOPES; MASS SPECTROMETRY; MICROBIOLOGY;

AEROBIC CONDITIONS; ANAEROBIC BIODEGRADATIONS; ANAEROBIC CONDITIONS; BATCH CULTURES; CONTAMINATED ENVIRONMENTS; EA-IRMS; ELEMENTAL ANALYZERS; ENRICHMENT FACTORS; EXTERNAL STANDARDS; ISOTOPE ANALYSIS; NATURAL ATTENUATIONS; PREPARATION METHODS; PRODUCTION SITES; STABLE ISOTOPES; STANDARD DEVIATIONS;

BIODEGRADATION;

CYCLONITE; NITROGEN 15; OXYGEN 18;

ANOXIC CONDITIONS; BIODEGRADATION; EXPLOSIVE; ISOTOPIC RATIO; NATURAL ATTENUATION; NITROGEN ISOTOPE; OXYGEN ISOTOPE; STABLE ISOTOPE;

ARTICLE; BIODEGRADATION; CHEMICAL ANALYSIS; ISOTOPE ANALYSIS; MASS SPECTROMETRY; POLLUTANT; THIN LAYER CHROMATOGRAPHY;

AEROBIOSIS; ANAEROBIOSIS; BIODEGRADATION, ENVIRONMENTAL; CHEMICAL FRACTIONATION; CHROMATOGRAPHY, THIN LAYER; NITROGEN ISOTOPES; OXYGEN ISOTOPES; REFERENCE STANDARDS; TRIAZINES;

EID: 55349095420     PISSN: 0013936X     EISSN: None     Source Type: Journal    
DOI: 10.1021/es8005942     Document Type: Article

References (38)

1. Spain, J. C. Biodegradation of nitroaromatic compounds. Annu. Rev. Microbiol. 1995, 523-555.
2. Hawari, J.; Beaudet, S.; Halasz, A.; Thiboutot, S.; Ampleman, G. Microbial degradation of explosives: biotransformation versus mineralization. Appl. Microbiol. Biotechnol. 2000, 54, 605-618.
3. Fournier, D.; Halasz, A.; Spain, J.; Fiurasek, P.; Hawaril, J. Determination of key metabolites during biodegradation of hexahydro-1,3,5- trinitro-1,3,5-triazine with Rhodococcus sp., strain DN22. Appl. Environ. Microbiol. 2002, 68, 166-172.
4. Bhushan, B.; Trott, S.; Spain, J. C.; Halasz, A.; Paquet, L.; Hawari, J. 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. 2003, 69, 1347-1351.
5. McCormick, N. G.; Cornell, J. H.; Kaplan, A. M. biodegradation of hexahydro-1,3,5-trinitro-1,3,5-triazine. Appl. Environ. Microbiol. 1981, 42, 817-823.
6. Hawari, J.; Halasz, A.; Sheremata, T.; Beaudet, S.; Groom, C.; Paquet, L.; Rhofir, C.; Ampleman, G.; Thiboutot, S. Characterization of metabolites during biodegradation of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) with municipal sludge. Appl. Environ. Microbiol. 2000, 66, 2652-2657.
7. Jackson, R. J.; Rylott, E. L.; Fournier, D.; Hawari, J.; Bruce, N. C. Exploring the biochemical properties and remediation applications of the unusual explosive-degrading P450 system XplA/B. Proc. Natl. Acad. Sci. U. S. A. 2007, 104, 16822-16827.
8. Binks, P. R.; Nicklin, S.; Bruce, N. C. Degradation of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) by Stenotrophomonas maltophilia PB1. Appl. Environ. Microbiol. 1995, 61, 1318-1322.
9. Coleman, N. V.; Nelson, D. R.; Duxbury, T. 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. 1998, 30, 1159-1167.
10. Nejidat, A.; Kafka, L.; Tekoah, Y.; Ronen, Z. Effect of organic and inorganic nitrogenous compounds on RDX degradation and cytochrome P-450 expression in Rhodococcus strain YH1. Biodegradation 2008, 19, 313-320.
11. Indest, K. J.; Crocker, F. H.; Athow, R. A TaqMan polymerase chain reaction method for monitoring RDX-degrading bacteria based on the xplA functional gene. J. Microbiol. Methods 2007, 68, 267-274.
12. Seth-Smith, H. M. B.; Rosser, S. J.; Basran, A.; Travis, E. R.; Dabbs, E. R.; Nicklin, S.; Bruce, N. C. Cloning, sequencing, and characterization of the Hexahydro-1,3,5-trinitro-1,3,5-triazine degradation gene cluster from Rhodococcus rhodochrous. Appl. Environ. Microbiol. 2002, 68, 4764-4771.
13. Sheremata, T. W.; Hawari, J. Mineralization of RDX by the white rot fungus Phanerochaete chrysosporium to carbon dioxide and nitrous oxide. Environ. Sci. Technol. 2000, 34, 3384-3388.
14. Bhatt, M.; Zhao, J. S.; Monteil-Rivera, F.; Hawari, J. Biodegradation of cyclic nitramines by tropical marine sediment bacteria. J. Ind. Microbiol. Biotechnol. 2005, 32, 261-267.
15. Van Aken, B.; Yoon, J. M.; Schnoor, J. L. Biodegradation of nitrosubstituted explosives 2,4,6-trinitrotoluene, hexahydro-1,3,5-trinitro-1,3, 5-triazine, and octahydro-1,3,5,7-tetranitro-1,3,5-tetrazocine by a phytosymbiotic Methylobacterium sp. associated with poplar tissues (Populus deltoides x nigra DN34). Appl. Environ. Microbiol. 2004, 70, 508-517.
16. Pennington, J. C.; Brannon, J. M.; Gunnison, D.; Harrelson, D. W.; Zakikhani, M.; Miyares, P.; Jenkins, T. F.; Clarke, J.; Hayes, C.; Ringleberg, D.; Perkins, E.; Fredrickson, H. Monitored natural attenuation of explosives. Soil Sed. Contam. 2001, 10, 45-70.
17. Griebler, C.; Safinowski, M.; Vieth, A.; Richnow, H. H.; Meckenstock, R. U. Combined application of stable carbon isotope analysis and specific metabolites determination for assessing in situ degradation of aromatic hydrocarbons in a tar oil-contaminated aquifer. Environ. Sci. Technol. 2004, 38, 617-631.
18. Meckenstock, R. U.; Morasch, B.; Griebler, C.; Richnow, H. H. Stable isotope fractionation analysis as a tool to monitor biodegradation in contaminated aquifers. J. Contam. Hydrol. 2004, 75, 215-255.
19. Elsner, M.; Zwank, L.; Hunkeler, D.; Schwarzenbach, R. P. A new concept linking observable stable isotope fractionation to transformation pathways of organic pollutants. Environ. Sci. Technol. 2005, 39, 6896-6916.
20. Richnow, H. H.; Annweiler, E.; Michaelis, W.; Meckenstock, R. U. Microbial in situ degradation of aromatic hydrocarbons in a contaminated aquifer monitored by carbon isotope fractionation. J. Contam. Hydrol. 2003, 65, 101-120.
21. Schmidt, T. C.; Zwank, L.; Elsner, M.; Berg, M.; Meckenstock, R. U.; Haderlein, S. B. Compound-specific stable isotope analysis of organic contaminants in natural environments: a critical review of the state of the art, prospects, and future challenges. Anal. Bioanal. Chem. 2004, 378, 283-300.
22. Phillips, S. A.; Doyle, S.; Philp, L.; Coleman, M. Proceedings: network developing forensic applications of stable isotope ratio mass spectrometry conference 2002. Sci. Justice 2003, 43, 153-160.
23. Lott, M. J.; Howa, J.; Ehleringer, J. R. Locating the Origins of Explosives through Stable Isotope Ratio Analysis. Poster at the Forensic Isotope Ratio Mass Spectrometry (Firms) Conference, 2002.
24. 15N of nitrate derived from explosive sources in karst aquifer beneath the Ammunition Burning Ground, Crane Naval Surface Warfare Center, Indiana, USA. J. Hydrol. 1998, 206, 164-175.
25. Bordeleau, G.; Savard, M. M.; Martel, R.; Ampleman, G.; Thiboutot, S. Determination of the origin of groundwater nitrate at an air weapons range using the dual isotope approach. J. Contam. Hydrol. 2008, 98, 97-105.
26. Beller, H. R.; Madrid, V.; Hudson, G. B.; McNab, W. W.; Carlsen, T. Biogeochemistry and natural attenuation of nitrate in groundwater at an explosives test facility. Appl. Geochem. 2004, 19, 1483-1494.
27. Hoffsommer, J. C.; Kubose, D. A.; Glover, D. J. Kinetic isotope effects and intermediate formation for the aqueous alkaline homogeneous hydrolysis of 1,3,5-tiaza-1,3,5-trinitrocyclohexane (RDX). J. Phys. Chem. 1977, 81, 380-385.
28. Brenner, A.; Ronen, Z.; Harel, Y.; Abeliovich, A. Use of RDX as a nitrogen source in biological treatment of munitions wastes. Water Environ. Res. 2000, 72, 469-475.
29. U.S. Environmental Protection Agency. Method 8330, SW-846 update III, Part 4: 1 (B), U.S. EPA Office of Solid Waste, U.S. Government Printing Office: Washington, DC, 1997.
30. Rayleigh, J. W. S. Theoretical considerations respecting the separation of gases by diffusion and similar processes. Philos. Mag. 1896, 42, 493-498.
31. Morasch, B.; Richnow, H. H.; Vieth, A.; Schink, B.; Meckenstock, R. U. Stable isotope fractionation caused by glycyl radical enzymes during bacterial degradation of aromatic compounds. Appl. Environ. Microbiol. 2004, 70, 2935-2940.
32. Melius, C. F., In Chemistry and Physics of Energetic Materials: Thermochemical Modeling: I Applications to Decomposition of Energetic Materials; Bulusu, S. N., Ed; Kluwer Academic Publishers: Dordrecht, Netherlands, 1990; pp 21-49.
33. Harris, N. J.; Lammertsma, K. Ab initio density functional computations of conformations and bond dissociation energies for hexahydro-1,3,5-trinitro-1, 3,5-triazine. J. Am. Chem. Soc. 1997, 119, 6583-6589.
34. Hengge, A. C.; Cleland, W. W. Phosphoryl-transfer reactions of phosphodiesters: characterization of transition states by heavy-atom isotope effects. J. Am. Chem. Soc. 1991, 113, 5835-5841.
35. Hengge, A. C. Isotope effects in the study of phosphoryl and sulfuryl transfer reactions. Acc. Chem. Res. 2002, 35, 105-112.
36. Hartenbach, A.; Hofstetter, T. B.; Berg, M.; Bolotin, J.; Schwarzenbach, R. P. Using nitrogen isotope fractionation to assess abiotic reduction of nitroaromatic compounds. Environ. Sci. Technol. 2006, 40, 7710-7716.
37. Tobler, N. B.; Hofstetter, T. B.; Schwarzenbach, R. P. Assessing iron-mediated oxidation of toluene and reduction of nitroaromatic contaminants in anoxic environments using compound-specific isotope analysis. Environ. Sci. Technol. 2007, 41, 7773-7780.
38. Hofstetter, T. B.; Neumann, A.; Arnold, W. A.; Bolotin, J.; Cramer, C. J.; Schwarzenbach, R. P. Substituent effects on nitrogen isotope fractionation during abiotic reduction of nitroaromatic compounds. Environ. Sci. Technol. 2008, 42, 1997-2003.