Abstract
Although a few aromatic compounds bearing one nitro group as a substituent are produced as secondary metabolites by microorganisms (31, 44, 45, 49) the majority of nitroaromatic compounds in the environment are due to anthropogenic activities. Nitrations are important reactions for the large-scale production of aminoaromatic structures that are synthons for pesticides, dyes, polymers, and pharmaceuticals. Nitroaromatic compounds such as nitrobenzene are used as solvents, whereas polynitroaromatic compounds serve as explosives. According to Hartter (16) 2,4,6-trinitrotoluene (TNT) is produced in amounts of 2 million pounds per year. Nitroaromatic compounds are therefore abundantly present in industrial waste streams and surface waters. 2,4,6-Trinitrotoluene is commonly found as the main contaminant of soil and ground water originating from facilities for manufacturing, processing, and disposing of explosives. Often these contaminants have leached from disposal lagoons into the surrounding soil, and in the case of military burdens of World War I and II, have contaminated the groundwater (13). Consequently, in Germany large areas of highly contaminated soils at former production plants must be remediated. TNT, its metabolites, and related compounds represent an environmental hazard because they exhibit considerable toxicity to humans, fish, algae, and microorganisms (39, 43, 50). Since incineration, the only proven technology for the destruction of explosives, is prohibitively costly, bioremediation represents an important alternative approach, which deserves to be considered.
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References
Beyer, H., and W. Walter. 1991. Lehrbuch der Organischen Chemie, 22th ed. S. Hirzel, Stuttgart.
Boopathy, R., C. F. Kulpa, and M. Wilson. 1993. Metabolism of 2,4,6-trinitrotoluene (TNT) by Desulfovibrio sp. (B strain). Appl. Microbiol. Biotechnol. 39:270–275.
Bruhn, C., H. Lenke, and H.-J. Knackmuss. 1987. Nitrosubstituted aromatic compounds as nitrogen source for bacteria. Appl. Environ. Microbiol. 53:208–210.
Corbett M. D., and B. R. Corbett. 1981. Metabolism of 4-chloronitrobenzene by the yeast Rhodosporidium sp. Appl. Environ. Microbiol. 41:942–949.
Dickel, O., and H.-J. Knackmuss. 1991. Catabolism of 1,3-dinitrobenzene by Rhodococcus sp. QT-1. Arch. Microbiol. 157:76–79.
Dickel, O., W. Haug, and H.-J. Knackmuss. 1993. Biodegradation of nitrobenzene by a sequential anaerobic-aerobic process. Biodegradation 4:187–194.
Duque, E., A. Haïdour, F. Godoy, and J. L. Ramos. 1993. Construction of a Pseudomonas hybrid strain that mineralizes 2,4,6-trinitrotoluene. J. Bacteriol. 175:2278–2283.
Ecker, S., T. Widmann, H. Lenke, O. Dickel, P. Fischer, C. Brunn, and H.-J. Knackmuss. 1992. Catabolism of 2,6-dinitrophenol by Alcaligenes eutrophus JMP134 and JMP222. Arch. Microbiol. 158:149–154.
Finley, K. T. 1974. The addition and substitution chemistry of quinones. In S. Patai (ed.) The chemistry of the quinonoid compounds. Pt. 2. J. Wiley & Sons, New York.
Funk, S. B., D. J. Roberts, D. L. Crawford, and R. L. Crawford. 1993. Initial phase optimization for bioremediation of munition compound-contaminated soils. Appl. Environ. Microbiol. 59:2171–2177.
Groenewegen, P. E. J., P. Breeuwen, J. M. L. M. v. Helvoort, A. A. M. Langenhoff, F. P. de Vries, and J. A. M. de Bont. 1992. Novel degradative pathway of 4-nitrobenzoate Comamonas acidovorans NBA-10. J. Gen. Microbiol. 13:1599–1605.
Groenewegen, P. E. J., and J. A. M. de Bont. 1992. Degradation of 4-nitrobenzoate via 4-hydroxylaminobenzoate and 3,4-dihydroxybenzoate in Comamonas acidovorans NBA-10. Arch. Microbiol. 158:381–386.
Haas, R., and E. v. Löw. 1986. Grundwasserbelastung durch eine Altlast. Die Folgen einer ehemaligen Sprengstoffproduktion für die heutige Trinkwassergewinnung. Forum Städte-Hygiene 37:33–43.
Haigier, B. E., and J. C. Spain. 1991. Biotransformation of nitrobenzene by bacteria containing toluene degradative pathways. Appl. Environ. Microbiol. 57:3156–3162.
Haigler, B. E., and J. C. Spain. 1993. Biodegradation of 4-nitrotoluene by Pseudomonas sp. strain 4NT. Appl. Environ. Microbiol. 59:2239–2243.
Hartter, D. R. 1985. The use and importance of nitroaromatic chemicals in the chemical industry, p. 1–14. In D. E. Rickert (ed.) Toxicity of nitroaromatic compounds. Chemical Industry Institute of Toxicology Series. Hemisphere Publishing Corp., New York.
Heijman, C. G., C. Holliger, M. A. Glaus, R. P. Schwarzenbach, and J. Zeyer. 1993. Abiotic reduction of 4-chloronitrobenzene to 4-chloroaniline in a dissimilatory iron-reducing enrichment culture. Appl. Environ. Microbiol. 59:4350–4353.
Hofmann, U. 1968. Aus der Chemie des Tons. Angew. Chem. I. E. 7:681.
Keys, L. D., and G. A. Hamilton. 1987. The mechanism for the conversion of a-amino-ß-carboxymuconate-8-semialdehyde to quinolinate, an apparent nonenzymic step in the biosynthesis of the nicotinamide coenzymes from tryptophan. J. Am. Chem. Soc. 109:2156–2163.
Lantz, R., and J. Gascon. 1965. Condensation oxydante de “l’éméraldine de Willstätter” avec l’aniline. Remarques concernant les réactions analogues génératrices de noirs d’aniline et la constitution de ces colorants. Bull. Soc. Chim. Fr. 816-821.
Lenke, H., and H.-J. Knackmuss. 1992. Initial hydrogenation during catabolism of picric acid by Rhodococcus erythropolis HL24-2. Appl. Environ. Microbiol. 58:2933–2937.
Lenke, H., D. H. Pieper, C. Bruhn, and H.-J. Knackmuss. 1992. Degradation of 2,4-dinitrophenol by two Rhodococcus erythropolis strain HL24-1 and HL24-2. Appl. Environ. Microbiol. 58:2928–2932.
Lenke, H., B. Wagener, G. Daun, and H.-J. Knackmuss. 1994. TNT-contaminated soil: a sequential anaerobic/aerobic process for bioremediation, abstr. Q-383, p. 456. Abstr. 94th Annu. Meet. Am. Soc. Microbiol. 1994.
Lewis, W. G., and E. Jamamoto. 1990. Lignin: occurrence, biogenesis and biodegradation. Ann. Rev. Plant Physiol. Plant Mol. Biol. 41:455–496.
March, J. 1985. Advanced Organic Chemistry, 3rd ed. J. Wiley & Sons, New York.
McCormick, N. G., F. E. Feeherry, and H. S. Levinson. 1976. Microbial transformation of 2,4,6-trinitrotoluene and other nitroaromatic compounds. Appl. Environ. Microbiol. 31:949–958.
Michels, J., and G. Gottschalk. 1994. Inhibition of the lignin peroxidase of Phanerochaete chrysosporium by hydroxylamino-dinitrotoluene, an early intermediate in the degradation of 2,4,6-trinitrotoluene. Appl. Environ. Microbiol. 60:187–194.
Mohilner, D. M., R. N. Adams, and W. J. Argasinger. 1962. Investigation of the kinetics and mechanism of the anodic oxidation of aniline in aqueous sulfuric acid solution at a platinum electrode. J. Am. Chem. Soc. 84:3618–3622.
Nishino, S. F., and J. C. Spain. 1993. Degradation of nitrobenzene by a Pseudomonas pseudoalcaligenes. Appl. Environ. Microbiol. 59:2520–2525.
Preuß, A., J. Fimpel, and G. Diekert. 1993. Anaerobic transformation of 2,4,6-trinitrotoluene (TNT). Arch. Microbiol. 159:345–353.
Raistrick, H. 1949. Chloromycetin: its structure and synthesis. Nature 163:5553–554.
Reineke, W., and H.-J. Knackmuss. 1978. Chemical structure and biodegradability of halogenated aromatic compounds. Substituent effects on 1,2-dioxygenation of benzoic acid. Biochim. Biophys. Acta 542:412–423.
Rhys-Williams, W., S. C. Taylor, and P. A. Williams. 1993. A novel pathway for the catabolism of 4-nitrotoluene by Pseudomonas. J. Gen. Microbiol. 139:1967–1972.
Rieger, P.-G., A. Preuss, V. Sinnwell, W. Francke, H. Lenke, and H.-J. Knackmuss. 1994. H-additions as initial steps of aerobic bacterial degradation of 2,4,6-trinitrophenol (picric acid), abstr. Q-120, p. 409. Abstr. 94th Annu. Meet. Am. Soc. Microbiol. 1994.
Scheffer, F., and P. Schachtschabel. 1989. Lehrbuch der Bodenkunde, p. 57, 12th ed. F. Enke, Stuttgart.
Sollenberger, P. Y., and R. B. Martin. 1968. Carbon-nitrogen and nitrogen-nitrogen double bond condensation reactions. In S. Patai (ed.) The chemistry of the amino group. J. Wiley & Sons, New York.
Spain, J. C., O. Wyss, and D. T. Gibson. 1979. Enzymatic oxidation of p-nitrophenol. Biochem. Biophys. Res. Commun. 88:634–641.
Spain, J. C., and D. T. Gibson. 1991. Pathway for biodégradation of p-nitrophenol in a Moraxella sp. Appl. Environ. Microbiol. 57:812–819.
Spanggord, R. J., K. E. Mortelmans, A. F. Griffing, and V. F. Simmon. 1982. Mutagenicity in Salmonella typhimurium and structure activity relationships of waste water components emanating from the manufacture of trinitrotoluene. Environ. Mutagen 4:163–179.
Spanggord, R. J., J. C. Spain, S. F. Nishino, and K. E. Mortelmans. 1991. Biodegradation of 2,4-dinitrotoluene by a Pseudomonas sp. Appl. Environ. Microbiol. 57:3200–3205.
Spiker, J. K., D. L. Crawford, and R. L. Crawford. 1992. Influence of 2,4,6-trinitrotoluene (TNT) concentrations on the degradation of TNT in explosive-contaminted soils by the white rot fungus Phanaerochaete chrysosporium. Appl. Environ. Microbiol. 58:3199–3202.
Stolz, A., B. Nörtemann, and H.-J. Knackmuss. 1992. Bacterial metabolism of 5-aminosalicylic acid. Initial ring cleavage. Biochem. J. 282:675–680.
Tan, E. L., C. H. Ho, W. H. Griest, and R. L. Tyndall. 1992. Mutagenicity of trinitrotoluene and its metabolites formed during composting. J. Toxicol. Environ. Health 36:165–175.
Van Pee, K. H., O. Salcher, and F. Lingens. 1981. Synthese von 7-Chlor-L-und 7-Chlor-D-tryptophan; Biosynthese von Pyrrolnitrin. Liebigs Ann. Chem. 2:233–239.
Vanulet J., and R. L. Van Etten. 1981. Biochemistry and pharmacology of the nitro and nitroso groups, p. 201–289. In H. Feuer (ed.) The chemistry of the nitro and nitroso groups. Krieger Publishing Company, New York.
Vorbeck, C., H. Lenke, P. Fischer, and H.-J. Knackmuss. 1994. Identification of ahydride Meisenheimer complex as a metabolite of 2,4,6-trinitrotoluene by a Mycobacterium sp. J. Bacteriol. 176:932–934.
Wagniere, G. H. 1981. Theoretical aspects of C-NO and C-NO2 bonds. In H. Feuer (ed.) The chemistry of the nitro and nitroso groups. Krieger Publishing Company, New York.
Weiss, A. 1963. Organische Derivate der glimmerartigen Schichtsilikate. Angew. Chem. 75:113–148.
Williams, M. C, and R. C. Barneby. 1977. The occurence of nitro-toxins in North American A stragalus (Fabaceae). Brittonia 29:310–326.
Won, W. D., L. H. Di Salvo, and J. Ng. 1976. Toxicity and mutagenicity of 2,4,6-trinitrotoluene and its microbial metabolites. Appl. Environ. Microbiol. 31:576–580.
Zeyer, J., and P. C. Kearney. 1984. Degradation of o-nitrophenol and m-nitrophenol by a Pseudomonas putida. J. Agric. Food Chem. 32:238–242.
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Rieger, PG., Knackmuss, HJ. (1995). Basic Knowledge and Perspectives on Biodegradation of 2,4,6-Trinitrotoluene and Related Nitroaromatic Compounds in Contaminated Soil. In: Spain, J.C. (eds) Biodegradation of Nitroaromatic Compounds. Environmental Science Research, vol 49. Springer, Boston, MA. https://doi.org/10.1007/978-1-4757-9447-2_1
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