Pathway of 2,4,6-Trinitrotoluene (TNT) Degradation by Phanerochaete Chrysosporium

Michels, Jochen; Gottschalk, Gerhard

doi:10.1007/978-1-4757-9447-2_9

Cited by 26 publications

(28 citation statements)

References 48 publications

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“…Because activity was detected in the detergent-solubilized form, where a membrane potential could not be maintained, a membrane potential redox system was assumed to be inessential for this reaction. On the other hand, NAD(P)H-dependent intracellular TNT reductase activity has also been described (151).…”

Section: Fungal Metabolism Of Tntmentioning

confidence: 99%

“…The mechanism by which the fungi mineralize the explosive is not known, but preliminary information about the process has been reported (107,151). When ligininolytic cultures of P. chrysosporium were incubated with 4-ADNT, a compound identified as 4-formamide-2,6-DNT was detected (Fig.…”

Section: Fungal Metabolism Of Tntmentioning

confidence: 99%

“…A number of reports on the mineralization of TNT by Phanerochaete chrysosporium and other fungi that mineralize TNT under ligninolytic conditions are available (47,107,129,151,164,183,194,196,(219)(220)(221)(235)(236)(237). Strict anaerobic bacteria of the genera Clostridium and Desulfovibrio (6) can degrade TNT via triaminotoluene, which might subsequently be metabolized to methylphloroglucinol and p-cresol, although conclusive biochemical evidence for this pathway is still needed (54,60,64,80,142,180).…”

Section: Introductionmentioning

confidence: 99%

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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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Section: Fungal Metabolism Of Tntmentioning

confidence: 99%

Section: Fungal Metabolism Of Tntmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Biological Degradation of 2,4,6-Trinitrotoluene

Esteve‐Núñez

Caballero

Ramos

2001

Microbiol Mol Biol Rev

421

287

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“…Today, it is a commonly accepted fact that the toxicity of aromatic amino and nitro compounds occurs via phase I reactions that yield arylhydroxylamine and nitrosoarene intermediates (58,130). These phase I reactions are the N-oxidation of amino groups and the reduction of nitro groups.…”

Section: Relevance Of Arylhydroxylamino and Nitroso Toxicity To The Tmentioning

confidence: 99%

“…The complete reduction of a single nitro group requires a six-electron transfer to form an amino group (11,107). The reduction pathway proceeds sequentially via the partially reduced nitrosoarene and arylhydroxylamine intermediates that are considered to be highly reactive in nature (29,58). The nitroso and hydroxylamino functional groups exist in what can be considered a "pseudo redox equilibrium" due to the insignificant kinetic barrier for the interconversion between these two functionalities (30).…”

Section: Introductionmentioning

confidence: 99%

Novel Pathways of Nitroaromatic Metabolism: Hydroxylamine Formation, Reactivity and Potential for Ring Fission for Destruction of TNT-CU1214

Hughes¹

2005

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Public reporting burden for the collection of information is estimated to average 1 hour per response, including the time for reviewing instructions, searching existing data sources, gathering and maintaining the data needed, and completing and reviewing the collection of information. Send comments regarding this burden estimate or any other aspect of this collection of information, including suggestions for reducing this burden, to Washington Headquarters Services, Directorate for Information Operations and Reports, 1215 Jefferson Davis Highway, Suite 1204, Arlington VA 22202-4302. Respondents should be aware that notwithstanding any other provision of law, no person shall be subject to a penalty for failing to comply with a collection of information if it does not display a currently valid OMB control number. REPORT DATE15 SERDP SPONSOR/MONITOR'S REPORT NUMBER(S) DISTRIBUTION/AVAILABILITY STATEMENT Approved for public release, distribution unlimited SUPPLEMENTARY NOTESThe original document contains color images. ABSTRACTBioremediation has come into favor as the treatment of choice for munitions contamination because of the prohibitively high cost of the treatment alternative, incineration. To this end, this research was designed to provide information required for development of bioremediation systems to treat TNT contamination. This research investigated biological transformation of TNT with the primary goal of furthering the understanding of the fundamental biochemical mechanisms responsible for transformation of TNT and its fate in the environment. This research explored the products of novel TNT transformation pathways and determined the mechanisms of TNT transformation and identified the enzymes responsible. Prescribed by This report was prepared under contract to the Department of Defense Strategic Environmental Research and Development Program (SERDP). The publication of this report does not indicate endorsement by the Department of Defense, nor should the contents be construed as reflecting the official policy or position of the Department of Defense. Reference herein to any specific commercial product, process, or service by trade name, trademark, manufacturer, or otherwise, does not necessarily constitute or imply its endorsement, recommendation, or favoring by the Department of Defense.ii Table of Contents Table of Contents ii List of Acronyms iv List of Figures vList of Tables vii Acknowledgements viii Executive Summary 1Objective 7Background 8 Aerobic Biodegradation 11Reductive Cometabolism 17Anaerobic-Aerobic Treatment of TNT 21 Materials and Methods 23Bacteria and culture methods 23Transformation of TNT 23 Analytical Methods 24Metabolite purification 24 Preparation of DHANT 25Protein extraction and fractionation 25Enzyme assays 26 Results and Accomplishments 27Novel metabolic products in TNT transformation pathway 27Transformation of TNT by Clostridium acetobutylicum 27Transformation of TNT by P. pseudoalcaligenes JS52 28Characterization of mechanism and enzymes responsible for TNT trans...

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