Aerobic Gram-Positive and Gram-Negative Bacteria Exhibit Differential Sensitivity to and Transformation of 2,4,6-Trinitrotoluene (TNT)

Fuller, Mark E.; Manning, John F.

doi:10.1007/s002849900216

Cited by 66 publications

(52 citation statements)

References 24 publications

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“…These chemicals have multiple applications in the synthesis of polyurethane foams, herbicides, insecticides, pharmaceuticals, and explosives (99), all of which are more recalcitrant than the raw material from which they are synthesized. Comprenhensive reviews of catabolic pathways leading to the degradation of nitroaromatic compounds are available (27,53,54,79,87,88,106,122,123,141,147,170,(210)(211)(212)243).…”

Section: Introductionmentioning

confidence: 99%

Biological Degradation of 2,4,6-Trinitrotoluene

Esteve‐Núñez

Caballero

Ramos

2001

Microbiol Mol Biol Rev

419

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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Section: Introductionmentioning

confidence: 99%

Biological Degradation of 2,4,6-Trinitrotoluene

Esteve‐Núñez

Caballero

Ramos

2001

Microbiol Mol Biol Rev

419

287

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“…Nevertheless, some Grampositive bacteria, such as members of the genera Corynebacterium, Rhodococcus and Streptomyces, are able to mineralize a wide array of aromatic compounds 2,13,15,19,20,28,34) . Comparative studies indicated that there are extensive differences between the biodegradation processes in Grampositive and Gram-negative bacteria 3,9,12,14,16,19,25,27) . However, our understanding of the aromatic degradation in Grampositive bacteria at the genetic and biochemical levels is relatively limited.…”

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confidence: 99%

“…Several Corynebacterium species isolated from soil are able to degrade styrenes 20) , 2,4-dichlorobenzoate 28) , 2,4,6-trinitrotoluene 14) or other aromatic compounds 5,7,10,34) . Our previous studies demonstrated that C. glutamicum could use different aromatic compounds as a sole source of carbon and energy and, multiple ring cleavage pathways might occur in this bacterium [31][32][33] .…”

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confidence: 99%

Genomic Analysis and Identification of Catabolic Pathways for Aromatic Compounds in Corynebacterium glutamicum

2005

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The catabolism of aromatic compounds in Corynebacterium glutamicum was investigated by genome data mining and by experimental analysis. Results indicated that C. glutamicum assimilated different aromatic compounds such as phenol, p-cresol, benzoate, 4-hydroxybenzoate, vanillate, vanillin, resorcinol, 3,5-dihydroxytoluene and 2,4-dihydroxybenzoate. Genome data indicated, and enzyme assays confirmed; the existence of multiple ring-cleavage pathways for the catabolism of central aromatic intermediates; the protocatechuate and catechol branches of the -ketoadipate pathway, two similar hydroxyquinol pathways and the gentisate pathway. Two putative hydroxyquinol 1,2-dioxygenase genes (ncg11113 and ncg12951) were cloned and functionally identified in Escherichia coli. The genes encoding enzymes for the conversion of phenol, benzoate, 3-hydroxybenzoate, 4-hydroxybenzoate and vanillate in the central -ketoadipate pathways were mapped on the chromosome of C. glutamicum. A unique 30-kb (approximately 1% of the entire genome) catabolic island that channels the degradation of various aromatic compounds was mapped to position 2525-2555 kb of the genome. The global analysis and characterization of aromatic degradation pathways provided new insights into the metabolic ability of C. glutamicum in addition to its well-known ability to produce various amino acids and vitamins.

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“…Growth experiments revealed that strain JS71 used 3 mol of nitrogen per mol of CL-20. 4,6,8,10,4,6,8,10,) is a new, highly energetic explosive related to the explosives RDX (hexahydro-1,3,5-trinitro-1,3,5-triazine) and HMX (octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine) (Fig. 1).…”

mentioning

confidence: 99%

Biodegradation of the Nitramine Explosive CL-20

Trott¹,

Nishino²,

Hawari

et al. 2003

Appl Environ Microbiol

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The cyclic nitramine explosive CL-20 (2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane) was examined in soil microcosms to determine whether it is biodegradable. CL-20 was incubated with a variety of soils. The explosive disappeared in all microcosms except the controls in which microbial activity had been inhibited. CL-20 was degraded most rapidly in garden soil. After 2 days of incubation, about 80% of the initial CL-20 had disappeared. A CL-20-degrading bacterial strain, Agrobacterium sp. strain JS71, was isolated from enrichment cultures containing garden soil as an inoculum, succinate as a carbon source, and CL-20 as a nitrogen source. Growth experiments revealed that strain JS71 used 3 mol of nitrogen per mol of CL-20. 4,6,8,10,4,6,8,10,) is a new, highly energetic explosive related to the explosives RDX (hexahydro-1,3,5-trinitro-1,3,5-triazine) and HMX (octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine) (Fig. 1). Due to its higher energy and its moderate sensitivity, CL-20 is expected to replace earlier explosives (19,20,22,25). The production of CL-20 and its use in munitions and propellants can be expected to lead to environmental contamination. RDX and HMX, common contaminants in soil and groundwater at munition manufacturing sites and firing ranges, are toxic and possibly carcinogenic (7,8,11,12,16,23,27). Because of the structural similarity of CL-20 to RDX and HMX, it is likely that CL-20 has similar effects. So far, there is little information available about the properties of CL-20. In contrast to RDX and HMX, CL-20 is a caged molecule (Fig. 1). The water solubility of CL-20 is 4.8 mg/liter at 25°C (Stevens Institute of Technology [http://www.cee.stevens-tech.edu/ResProj.html]), which is lower than the solubility of the nitramines RDX and HMX (38.4 and 6.6 mg/liter at 20°C, respectively) (27).The microbial degradation of RDX and HMX under aerobic and anaerobic conditions has been extensively investigated (1, 2, 4-6, 9, 13-15, 17, 21). Under anaerobic conditions, three degradation pathways have been proposed. The first includes the production of nitroso derivatives of RDX and HMX, which are subject to further degradation (15, 21). Hawari et al. suggested a second degradation pathway which includes the direct ring cleavage of RDX and HMX without the initial reduction of the nitro groups (14, 15). The third proposed degradation pathway is based on N denitration prior to ring cleavage (1).Under aerobic conditions, RDX is degraded by a yet-unknown mechanism. The initial attack seems to be catalyzed by a cytochrome P450 (1a, 6, 24). RDX degradation by Rhodococcus sp. strain DN22 leads to the formation of nitrite, nitrous oxide, ammonia, formaldehyde, and a dead-end product with a molecular weight of 119 which was recently identified as 4-nitro-2,4-diazabutanal (1a, 5, 9). Fournier et al. proposed a degradation pathway which includes an initial denitration of RDX followed by ring cleavage to formaldehyde and the dead-end product (9).To the best of our knowledge, no biodegradation of CL-20 has...

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Aerobic Gram-Positive and Gram-Negative Bacteria Exhibit Differential Sensitivity to and Transformation of 2,4,6-Trinitrotoluene (TNT)

Cited by 66 publications

References 24 publications

Biological Degradation of 2,4,6-Trinitrotoluene

Biological Degradation of 2,4,6-Trinitrotoluene

Genomic Analysis and Identification of Catabolic Pathways for Aromatic Compounds in Corynebacterium glutamicum

Biodegradation of the Nitramine Explosive CL-20

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