Biotransformation Patterns of 2,4,6-Trinitrotoluene by Aerobic Bacteria

Kalafut, Tim; Wales, Melinda E.; Rastogi, Vipin K.; Naumova, R. P.; Zaripova, S. K.; Wild, James R.

doi:10.1007/s002849900278

Cited by 93 publications

(72 citation statements)

References 30 publications

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“…In aerobic systems, partially reduced products accumulate. The predominant products under aerobic conditions are the aminodinitrotoluene (ADNT) isomers and, to a lesser extent, 2,4-diamino-6-nitrotoluene and azoxytetranitrotoluenes (4,5,12,17,24,39). A productive reduction of TNT is catalyzed by the nitrate ester reductase from Enterobacter cloacae PB2.…”

mentioning

confidence: 99%

Oxidative Transformation of Aminodinitrotoluene Isomers by Multicomponent Dioxygenases

Johnson¹,

Smets

Spain³

2001

Appl Environ Microbiol

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The electron-withdrawing nitro substituents of 2,4,6-trinitrotoluene (TNT) make the aromatic ring highly resistant to oxidative transformation. The typical biological transformation of TNT involves reduction of one or more of the nitro groups of the ring to produce the corresponding amine. Reduction of a single nitro substituent of TNT to an amino substituent increases the electron density of the aromatic nucleus considerably. The comparatively electron-dense nuclei of the aminodinitrotoluene (ADNT) isomers would be expected to be more susceptible to oxygenase attack than TNT. The hypothesis was tested by evaluating three nitroarene dioxygenases for the ability to hydroxylate the ADNT isomers. The predominant reaction was dioxygenation of the ring to yield nitrite and the corresponding aminomethylnitrocatechol. A secondary reaction was benzylic monooxygenation to form aminodinitrobenzyl alcohol. The substrate preferences and catalytic specificities of the three enzymes differed considerably. The discovery that the ADNT isomers are substrates for the nitroarene dioxygenases reveals the potential for extensive bacterial transformation of TNT under aerobic conditions.

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mentioning

confidence: 99%

Oxidative Transformation of Aminodinitrotoluene Isomers by Multicomponent Dioxygenases

Johnson¹,

Smets

Spain³

2001

Appl Environ Microbiol

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“…Recently, Kalafut et al (121) reported a promising aerobic route for TNT metabolism which led to the production of 2-amino-4-nitrotoluene. This metabolite results from the loss of one of the original nitro groups, leaving two adjacent unsubstituted carbon atoms that can serve as a substrate for oxygenases.…”

Section: Aerobic Metabolism Of Tnt By Bacteriamentioning

confidence: 99%

Biological Degradation of 2,4,6-Trinitrotoluene

Esteve‐Núñez

Caballero

Ramos

2001

Microbiol Mol Biol Rev

421

287

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Nitroaromatic compounds are xenobiotics that have found multiple applications in the synthesis of foams, pharmaceuticals, pesticides, and explosives. These compounds are toxic and recalcitrant and are degraded relatively slowly in the environment by microorganisms. 2,4,6-Trinitrotoluene (TNT) is the most widely used nitroaromatic compound. Certain strains of Pseudomonas and fungi can use TNT as a nitrogen source through the removal of nitrogen as nitrite from TNT under aerobic conditions and the further reduction of the released nitrite to ammonium, which is incorporated into carbon skeletons. Phanerochaete chrysosporium and other fungi mineralize TNT under ligninolytic conditions by converting it into reduced TNT intermediates, which are excreted to the external milieu, where they are substrates for ligninolytic enzymes. Most if not all aerobic microorganisms reduce TNT to the corresponding amino derivatives via the formation of nitroso and hydroxylamine intermediates. Condensation of the latter compounds yields highly recalcitrant azoxytetranitrotoluenes. Anaerobic microorganisms can also degrade TNT through different pathways. One pathway, found in Desulfovibrio and Clostridium, involves reduction of TNT to triaminotoluene; subsequent steps are still not known. Some Clostridium species may reduce TNT to hydroxylaminodinitrotoluenes, which are then further metabolized. Another pathway has been described in Pseudomonas sp. strain JLR11 and involves nitrite release and further reduction to ammonium, with almost 85% of the N-TNT incorporated as organic N in the cells. It was recently reported that in this strain TNT can serve as a final electron acceptor in respiratory chains and that the reduction of TNT is coupled to ATP synthesis. In this review we also discuss a number of biotechnological applications of bacteria and fungi, including slurry reactors, composting, and land farming, to remove TNT from polluted soils. These treatments have been designed to achieve mineralization or reduction of TNT and immobilization of its amino derivatives on humic material. These approaches are highly efficient in removing TNT, and increasing amounts of research into the potential usefulness of phytoremediation, rhizophytoremediation, and transgenic plants with bacterial genes for TNT removal are being done

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“…Several researchers have reported TNT degradation by aerobic bacteria, which use denitration pathway [2,4,20,21] and showed that TNT denitration is profitable to bacteria. [22,23] The level of denitration was substantially higher in static cultures than in orbital shaken cultures (data not shown).…”

Section: Discussionmentioning

confidence: 99%

“…Under many typical setting the rates of degradation are limited, mainly due to the accumulation of intermediate metabolites, and their toxic effects on biological systems. [2] The investigators from various places have isolated several organisms, which degrade explosive aerobically. Most notable among them are Stenotrophomonas, [7] Rhodococcus, [8,9] Enterobacter, [5] Pseudomonas, [10] Mycobacterium, [11] Bacillus, [2] Serratia [12] and Staphylococcus, [2] Halasz et al [13] have reported detection of degradation of explosives by soil indigenous organisms.…”

mentioning

confidence: 99%

“…Numerous cases of munitions workers reportedly developed liver damage and anaemia owing to TNT exposure. [2] Bioremediation offers as attractive and economic way of removal of explosives from contaminated sites. [3] Number of bacteria and fungi are able to utilize TNT [4] as a nitrogen source by removing nitrogen under either aerobic [5] or anaerobic conditions.…”

mentioning

confidence: 99%

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TNT biotransformation potential of the clinical isolate of Salmonella typhimurium - potential ecological implications

Litake

Joshi

Ghole

2005

Indian J Occup Environ Med

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Out of fifty-six isolates screened three bacterial strains enriched with TNT either as sole source of nitrogen (for Salmonella typhimurium, Klebsiella pneumoniae) or along with co-substrate (for Acinetobacter baumannii), have been carried out nitro group reduction under aerobic conditions. During studies, S. typhimurium found to have high potential (100% of 50 mg l , in presence of co-substrate). Therefore studies were focused on S. typhimurium, which had shown good growth, and protein contents, with disappearance of TNT, and concomitantly release of nitrite over the period of time. Removal of TNT was analyzed by HPLC, and nitrite liberation was consistently found coincided with TNT disappearance from the medium. As compared to earlier reports, 100% disappearance of TNT within 30 h by S. typhimurium is encouraging, and may indicate its potential in bioremediation of TNT. This is the first report on S. typhimurium, Klebsiella pneumoniae and Acinetobacter baumannii for transformation of TNT with nitrite release into the medium.

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Biotransformation Patterns of 2,4,6-Trinitrotoluene by Aerobic Bacteria

Cited by 93 publications

References 30 publications

Oxidative Transformation of Aminodinitrotoluene Isomers by Multicomponent Dioxygenases

Oxidative Transformation of Aminodinitrotoluene Isomers by Multicomponent Dioxygenases

Biological Degradation of 2,4,6-Trinitrotoluene

TNT biotransformation potential of the clinical isolate of Salmonella typhimurium - potential ecological implications

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