Abstract
Aerobic and anoxic biotransformation of 2,4-dinitrotoluene (DNT) was examined by using a Pseudomonas aeruginosa strain isolated from a plant treating propellant manufacturing wastewater. DNT biotransformation in the presence and absence of oxygen was mostly reductive and was representative of the type of cometabolic transformations that occur when a high concentration of an easily degradable carbon source is present. P. aeruginosa reduced both nitro groups on DNT, with the formation of mainly 4-amino-2-nitrotoluene and 2-amino-4-nitrotoluene and small quantities of 2,4-diaminotoluene. Acetylation of the arylamines was a significant reaction. 4-Acetamide-2-nitrotoluene and the novel compounds 2-acetamide-4-nitrotoluene, 4-acetamide-2-aminotoluene, and 2,4-diacetamidetoluene were identified as DNT metabolites. The biotransformation of 2,4-diaminotoluene to 4-acetamide-2-aminotoluene was 24 times faster than abiotic transformation. 2-Nitrotoluene and 4-nitrotoluene were also reduced to their corresponding toluidines and then acetylated. However, the yield of 4-acetamidetoluene was much higher than that of 2-acetamidetoluene, demonstrating that acetylation at the position para to the methyl group was favored.
Full Text
The Full Text of this article is available as a PDF (292.0 KB).
Selected References
These references are in PubMed. This may not be the complete list of references from this article.
- Duque E., Haidour A., Godoy F., Ramos J. L. Construction of a Pseudomonas hybrid strain that mineralizes 2,4,6-trinitrotoluene. J Bacteriol. 1993 Apr;175(8):2278–2283. doi: 10.1128/jb.175.8.2278-2283.1993. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Fernando T., Bumpus J. A., Aust S. D. Biodegradation of TNT (2,4,6-trinitrotoluene) by Phanerochaete chrysosporium. Appl Environ Microbiol. 1990 Jun;56(6):1666–1671. doi: 10.1128/aem.56.6.1666-1671.1990. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Funk S. B., Roberts D. J., Crawford D. L., Crawford R. L. Initial-phase optimization for bioremediation of munition compound-contaminated soils. Appl Environ Microbiol. 1993 Jul;59(7):2171–2177. doi: 10.1128/aem.59.7.2171-2177.1993. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Gilcrease P. C., Murphy V. G. Bioconversion of 2,4-diamino-6-nitrotoluene to a novel metabolite under anoxic and aerobic conditions. Appl Environ Microbiol. 1995 Dec;61(12):4209–4214. doi: 10.1128/aem.61.12.4209-4214.1995. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Haigler B. E., Spain J. C. Biodegradation of 4-nitrotoluene by Pseudomonas sp. strain 4NT. Appl Environ Microbiol. 1993 Jul;59(7):2239–2243. doi: 10.1128/aem.59.7.2239-2243.1993. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Hallas L. E., Alexander M. Microbial transformation of nitroaromatic compounds in sewage effluent. Appl Environ Microbiol. 1983 Apr;45(4):1234–1241. doi: 10.1128/aem.45.4.1234-1241.1983. [DOI] [PMC free article] [PubMed] [Google Scholar]
- McCormick N. G., Cornell J. H., Kaplan A. M. Identification of biotransformation products from 2,4-dinitrotoluene. Appl Environ Microbiol. 1978 May;35(5):945–948. doi: 10.1128/aem.35.5.945-948.1978. [DOI] [PMC free article] [PubMed] [Google Scholar]
- McCormick N. G., Feeherry F. E., Levinson H. S. Microbial transformation of 2,4,6-trinitrotoluene and other nitroaromatic compounds. Appl Environ Microbiol. 1976 Jun;31(6):949–958. doi: 10.1128/aem.31.6.949-958.1976. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Naumova R. P., Selivanovskaia S. Iu, Cherepneva I. E. Prevrashchenie 2,4,6-trinitrotoluola v usloviiakh kislorodnogo i nitratnogo dykhaniia Pseudomonas fluorescens. Prikl Biokhim Mikrobiol. 1988 Jul-Aug;24(4):493–498. [PubMed] [Google Scholar]
- Preuss A., Fimpel J., Diekert G. Anaerobic transformation of 2,4,6-trinitrotoluene (TNT). Arch Microbiol. 1993;159(4):345–353. doi: 10.1007/BF00290917. [DOI] [PubMed] [Google Scholar]
- Rhys-Williams W., Taylor S. C., Williams P. A. A novel pathway for the catabolism of 4-nitrotoluene by Pseudomonas. J Gen Microbiol. 1993 Sep;139(9):1967–1972. doi: 10.1099/00221287-139-9-1967. [DOI] [PubMed] [Google Scholar]
- Spanggord R. J., Spain J. C., Nishino S. F., Mortelmans K. E. Biodegradation of 2,4-dinitrotoluene by a Pseudomonas sp. Appl Environ Microbiol. 1991 Nov;57(11):3200–3205. doi: 10.1128/aem.57.11.3200-3205.1991. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Valli K., Brock B. J., Joshi D. K., Gold M. H. Degradation of 2,4-dinitrotoluene by the lignin-degrading fungus Phanerochaete chrysosporium. Appl Environ Microbiol. 1992 Jan;58(1):221–228. doi: 10.1128/aem.58.1.221-228.1992. [DOI] [PMC free article] [PubMed] [Google Scholar]