Identifying competing aerobic nitrobenzene biodegradation pathways by compound-specific isotope analysis

Environmental Science and Technology

Volumn 42, Issue 13, 2008, Pages 4764-4770

  Hofstetter, Thomas B ^a   Spain, Jim C ^b   Nishino, Shirley F ^b   Bolotin, Jakov ^a   Schwarzenbach, René P ^a  

^a ETH ZURICH   (Switzerland)

^b Georgia Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; BIOCHEMISTRY; BIODEGRADATION; GROUNDWATER; GROUNDWATER POLLUTION; HYDROGEOLOGY; NITROBENZENE; DEGRADATION; ISOTOPES; MICROBIOLOGY; NITROGEN COMPOUNDS; REACTION KINETICS;

AEROBIC (CSTR); AEROBIC CONDITIONS; COMPOUND SPECIFIC ISOTOPE ANALYSIS (CSIA); ISOTOPE ANALYSIS; NITROAROMATIC COMPOUNDS; NITROBENZENE OXIDATION; PARTIAL REDUCTION; REACTION PATHWAYS;

ISOTOPES; NITROBENZENE;

NITROBENZENE;

BIODEGRADATION; DEHYDRATION; IDENTIFICATION METHOD; ISOTOPIC ANALYSIS; LABORATORY METHOD; OXIC CONDITIONS; OXIDATION;

ARTICLE; BIODEGRADATION; BIOREMEDIATION; CHEMICAL REACTION; COMAMONAS; ISOTOPE ANALYSIS; OXIDATION; PSEUDOMONAS PSEUDOALCALIGENES; SOIL POLLUTANT; WATER POLLUTANT;

BIODEGRADATION, ENVIRONMENTAL; CARBON ISOTOPES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COMAMONAS; KINETICS; MASS SPECTROMETRY; MOLECULAR STRUCTURE; NITROBENZENES; NITROGEN ISOTOPES; OXIDATION-REDUCTION; PSEUDOMONAS PSEUDOALCALIGENES; SOIL POLLUTANTS;

COMAMONAS SP.; PSEUDOMONAS PSEUDOALCALIGENES;

AEROBIC CONDITION; APPARENT KINETICS; AROMATIC RINGS; BIODEGRADATION PATHWAYS; COMPOUND-SPECIFIC ISOTOPE ANALYSIS; CONTAMINATED ENVIRONMENT; DIOXYGENS; ISOTOPE ANALYSIS; ISOTOPE ENRICHMENTS; LABORATORY STUDIES; NITROAROMATIC COMPOUND; NITROBENZENE OXIDATION; NITROSOBENZENES; PARTIAL REDUCTION; RATE-LIMITING STEPS; TWO-ELECTRON REDUCTION;

EID: 46849110982     PISSN: 0013936X     EISSN: None     Source Type: Journal    
DOI: 10.1021/es8001053     Document Type: Article

References (46)

1. Spain, J. C.; Hughes, J. B.; Knackmuss, H.-J. Biodegradation of Nitroaromatic Compounds and Explosives, Lewis Publishers: Boca Raton, FL, 2000; p 434.
2. Nishino, S. F.; Spain, J. C. Catabolism of nitroaromatic compounds. In Pseudomonas, Vol. 3: Biosynthesis of Macromolecules and Molecular Metabolism; Ramos, J. L., Ed.; Kluwer Academic/Plenum Publishers: New York, 2004; pp 575-608.
3. Rügge, K.; Hofstetter, T. B.; Haderlein, S. B.; Bjerg, P. L.; Knudsen, S.; Zraunig, C.; Mosbæk, H.; Christensen, T. H. Characterization of predominant reductants in an anaerobic leachate-affected aquifer by nitroaromatic probe compounds. Environ. Sci. Technol. 1998, 32 (1), 23-31.
4. Haderlein, S. B., Hofstetter, T. B., Schwarzenbach, R. P. Subsurface chemistry of nitroaromatic compounds. In Biodegradation of Nitroaromatic Compounds and Explosives, Spain, J. C., Hughes, J. B., Knackmuss, H.-J., Eds.; Lewis Publishers: Boca Raton, FL, 2000; pp 311-356.
5. Nishino, S. F.; Spain, J. C.; He, Z. Strategies for aerobic degradation of nitroaromatic compounds by bacteria: Process discovery to field applications. In Biodegradation of Nitroaromatic Compounds and Explosives, Spain, J. C., Hughes, J. B., Knackmuss, H.-J., Eds.; Lewis Publishers: Boca Raton, FL, 2000; pp 7-61.
6. Nishino, S. F.; Spain, J. C. Oxidative pathway for the biodegradation of nitrobenzene by Comamonas sp. Strain JS765. Appl. Environ. Microbiol. 1995, 61 (6), 2308-2313.
7. Spain, J. C.; Gibson, D. T. Pathway for biodegradation of para-nitrophenol in a Moraxella sp. Appl. Environ. Microbiol. 1991, 57 (3), 812-819.
8. Vorbeck, C.; Lenke, H.; Fischer, P.; Knackmuss, H.-J. Identification of a hydride-Meisenheimer complex as a metabolite of 2,4,6-trinitrotoluene by a Mycobacterium strain. J. Bacteriol. 1994, 176 (3), 932-934.
9. Vorbeck, C.; Lenke, H.; Fischer, P.; Spain, J. C.; Knackmuss, H.-J. Initial reductive reactions in aerobic microbial metabolism of 2,4,6-trinitrotoluene. Appl. Environ. Microbiol. 1998, 64 (1), 246-252.
10. Nishino, S. F.; Spain, J. C. Degradation of nitrobenzene by a Pseudomonas pseudoalcaligenes. Appl. Environ. Microbiol. 1993, 59 (8), 2520-2525.
11. Friemann, R.; Ivkovic-Jensen, M. M.; Lessner, D. J.; Yu, C. L.; Gibson, D. T.; Parales, R. E.; Eklund, H.; Ramaswamy, S. Structural insight into the dioxygenation of nitroarene compounds: the crystal structure of nitrobenzene dioxygenase. J. Mol. Biol. 2005, 348 (5), 1139-1151.
12. Berg, M.; Bolotin, J.; Hofstetter, T. B. Compound-specific nitrogen and carbon isotope analysis of nitroaromatic compounds in aqueous samples using solid-phase microextraction coupled to GC/IRMS. Anal. Chem. 2007, 79 (6), 2386-2393.
13. 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 (24), 7710-7716.
14. 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 (22), 7773-7780.
15. Hofstetter, T. B.; Neumann, A.; Arnold, W. A.; Hartenbach, A. E.; 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 (6), 1997-2003.
16. Zwank, L.; Berg, M.; Elsner, M.; Schmidt, T. C.; Schwarzenbach, R. P.; Haderlein, S. B. New evaluation scheme for two-dimensional isotope analysis to decipher biodegradation processes: Application to groundwater contamination by MTBE. Environ. Sci. Technol. 2005, 39 (4), 1018-1029.
17. 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 (18), 6896-6916.
18. Melander, L.; Saunders, W. H. Reaction Rates of Isotopic Molecules; John Wiley & Sons: New York, 1980.
19. Kuder, T.; Wilson, J. T.; Kaiser, P.; Kolhatkar, R.; Philp, P.; Allen, J. Enrichment of stable carbon and hydrogen isotopes during anaerobic biodegradation of MTBE: Microcosm and field evidence. Environ. Sci. Technol. 2005, 39 (1), 213-220.
20. Elsner, M.; McKelvie, J.; Lacrampe-Couloume, G.; Sherwood Lollar, B. Insight into methyl tert-butyl ether (MTBE) stable isotope fractionation from abiotic reference experiments. Environ. Sci. Technol. 2007, 41 (16), 5693-5700.
21. Hofstetter, T. B.; Reddy, C. M.; Heraty, L. J.; Berg, M.; Sturchio, N. C. Carbon and chlorine isotope effects during abiotic reductive dechlorination of polychlorinated ethanes. Environ. Sci. Technol. 2007, 41 (13), 4662-4668.
22. Hunkeler, D.; Aravena, R.; Berry-Spark, K.; Cox, E. Assessment of degradation pathways in an aquifer with mixed chlorinated hydrocarbon contamination using stable isotope analysis. Environ. Sci. Technol. 2005, 39 (16), 5975-5981.
23. Hirschorn, S. K.; Dinglasan, M. J.; Elsner, M.; Mancini, S. A.; Lacrampe-Couloume, G.; Edwards, E. A.; Sherwood Lollar, B. Pathway dependent isotopic fractionation during aerobic biodegradation of 1,2-dichloroethane. Environ. Sci. Technol. 2004, 38 (18), 4775-4781.
24. Chartrand, M. M. G.; Waller, A.; Mattes, T. E.; Elsner, M.; Lacrampe-Couloume, G.; Gossett, J. M.; Edwards, E. A.; Sherwood Lollar, B. Carbon isotopic fractionation during aerobic vinyl chloride degradation. Environ. Sci. Technol. 2005, 39 (4), 1064-1070.
25. Morasch, B.; Richnow, H. H.; Schink, B.; Vieth, A.; Meckenstock, R. U. Carbon and hydrogen stable isotope fractionation during aerobic bacterial degradation of aromatic hydrocarbons. Appl. Environ. Microbiol. 2002, 68 (10), 5191-5194.
26. Northrop, D. B. The expression of isotope effects on enzyme-catalyzed reactions. Annu. Rev. Biochem. 1981, 50, 103-131.
27. Cook, P. F. Enzyme Mechanism from Isotope Effects, CRC Press: Boca Raton, FL, 1991.
28. Sturchio, N. C.; Bohlke, J. K.; Beloso, A. D.; Streger, S. H.; Heraty, L. J.; Hatzinger, P. B. Oxygen and chlorine isotopic fractionation during perchlorate biodegradation: laboratory results and implications for forensics and natural attenuation studies. Environ. Sci. Technol. 2007, 41 (8), 2796-2802.
29. Van Breukelen, B. M. Extending the Rayleigh equation to allow competing isotope fractionating pathways to improve quantification of biodegradation. Environ. Sci. Technol. 2007, 41 (11), 4004-4010.
30. Bruhn, C.; Lenke, H.; Knackmuss, H.-J. Nitrosubstituted aromatic compounds as nitrogen source for bacteria. Appl. Environ. Microbiol. 1987, 53 (1), 208-210.
31. Hofstetter, T. B.; Heijman, C. G.; Haderlein, S. B.; Holliger, C.; Schwarzenbach, R. P. Complete reduction of TNT and other (poly)nitroaromatic compounds under iron reducing subsurface conditions. Environ. Sci. Technol. 1999, 33 (9), 1479-1487.
32. Sherwood Lollar, B.; Hirschorn, S. K.; Chartrand, M. M. G.; Lacrampe-Couloume, G. An approach for assessing total instrumental uncertainty in compound-specific carbon isotope analysis: Implications for environmental remediation studies. Anal. Chem.. 2007, 79 (9), 3469-3475.
33. Scott, K. M.; Lu, X.; Cavanaugh, C. M.; Liu, J. S. Optimal methods for estimating kinetic isotope effects from different forms of the Rayleigh distillation equation. Geochim. Cosmochim. Acta 2004, 68 (3), 433-442.
34. Lessner, D. J.; Johnson, G. R.; Parales, R. E.; Spain, J. C.; Gibson, D. T. Molecular characterization and substrate specificity of nitrobenzene dioxygenase from Comamonas sp. strain JS765. Appl. Environ. Microbiol. 2002, 68 (2), 634-641.
35. He, Z.; Spain, J. C. Comparison of the downstream pathways for degradation of nitrobenzene by Pseudomonas pseudoalcaligenes JS45 (2-aminophenol pathway) and by Comamonas sp. JS765 (catechol pathway). Arch. Microbiol. 1999, 171 (5), 309-316.
36. Boyd, D. R.; Bugg, T. D. H. Arene cis-dihydrodiol formation: from biology to application. Org. Biomol. Chem. 2006, 4 (2), 181-192.
37. Houk, K. N.; Strassner, T. Establishing the (3 + 2) mechanism for the permanganate oxidation of alkenes by theory and kinetic isotope effects. J. Org. Chem. 1999, 64 (3), 800-802.
38. DelMonte, A. J.; Haller, J.; Houk, K. N.; Sharpless, K. B.; Singleton, D. A.; Strassner, T.; Thomas, A. A. Experimental and theoretical kinetic isotope effects for asymmetric dihydroxylation. Evidence supporting a rate-limiting "(3 + 2)" cycloaddition. J. Am. Chem. Soc. 1997, 119 (41), 9907-9908.
39. Singleton, D. A.; Merrigan, S. R.; Liu, J.; Houk, K. N. Experimental geometry of the epoxidation transition state. J. Am. Chem. Soc. 1997, 119 (14), 3385-3386.
40. Nadeau, L. J.; He, Z.; Spain, J. C. Bacterial conversion of hydroxylamino aromatic compounds by both lyase and mutase enzymes involves intramolecular transfer of hydroxyl groups. Appl. Environ. Microbiol. 2003, 69 (5), 2786-2793.
41. 0 =-6 and pH 9.6. J. Electroanal. Chem. 1992, 341 (1-2), 227-255.
42. Somerville, C. C.; Nishino, S. F.; Spain, J. C. Purification and characterization of nitrobenzene nitroreductase from Pseudomonas pseudoalcaligenes JS45. J. Bacteriol. 1995, 177 (13), 3837-3842.
43. Boon, N.; Goris, J.; De Vos, P.; Verstraete, W.; Top, E. M. Genetic diversity among 3-chloroaniline- and aniline-degrading strains of the Comamonadaceae. Appl. Environ. Microbiol. 2001, 67 (3), 1107-1115.
44. Urata, M.; Uchida, E.; Nojiri, H.; Omori, T.; Obo, R.; Miyaura, N.; Ouchiyama, N. Genes involved in aniline degradation by Delftia acidovorans strain 7N and its distribution in the natural environment. Biosci., Biotechnol., Biochem. 2004, 68 (12), 2457-2465.
45. Swindoll, C. M.; Perkins, R. E.; Gannon, J. T.; Holmes, M.; Fisher, G. A. Assessment of bioremediation of a contaminated wetland. In Intrinsic Bioremediation; Hinchee, R. E., Wilson, J. T., Downey, D. C., Eds.; Battelle Press: Columbus, OH, 1995; Vol. 3, pp 163-169.
46. Dickel, O.; Haug, W.; Knackmuss, H.-J. Biodegradation of nitrobenzene by a sequential anaerobic-aerobic process. Biodegradation 1993, 4 (3), 187-194.