Bioelimination of trinitroaromatic compounds: immobilization versus mineralization

Heiss, Gesche; Knackmuss, Hans‐Joachim

doi:10.1016/s1369-5274(02)00316-8

Cited by 55 publications

(55 citation statements)

References 28 publications

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“…The degradation of TNT by microorganisms has been extensively studied for many years and the results have been compiled in numerous reviews (Fritsche et al 2000;Hawari et al 2000;Lenke et al 2000;Spain et al 2000;Esteve-Núñez et al 2001;Rodgers and Bunce 2001;Rosser et al 2001;van Aken and Agathos 2001;Heiss and Knackmus 2002;Fuller et al 2004;Lewis et al 2004;Schrader and Hess 2004;Zhao et al 2004;Stenuit and Agathos 2010;Rylott et al 2011). Some basic reactions are listed in Table 1.…”

Section: Microbial Degradation Of Tntmentioning

confidence: 99%

“…Almost 85 % of the nitrogen of TNT can be incorporated into the cells as organic nitrogen (Esteve-Núñez and Ramos 1998;Esteve-Núñez et al 2000). As an intermediate of nitrogen release, Meisenheimer-complexes have been identified (French et al 1998;Heiss and Knackmus 2002). It has been proposed that the dihydride-complex slowly rearomatizes with the concomitant release of nitrite.…”

Section: Tnt As a Source Of Nitrogen Or Electron Acceptormentioning

confidence: 99%

“…However, TNT is resistant to oxidative microbial degradation and only low mineralization rates have been sporadically reported with bacterial consortia and several white-rot fungi. The reason is the presence of three electron withdrawing nitro-groups in TNT which introduce steric constraints and confer a high electron deficiency to the aromatic ring (Heiss and Knackmus 2002). Instead of oxidation, many bacteria catalyse the reduction of one or two nitro-groups of TNT to monoaminodinitrotoluenes (ADNT) and diaminonitrotoluenes (DANT).…”

Section: Introductionmentioning

confidence: 99%

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Microbial Degradation of 2,4,6-Trinitrotoluene In Vitro and in Natural Environments

Claus

2013

Environmental Science and Engineering

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Section: Microbial Degradation Of Tntmentioning

confidence: 99%

Section: Tnt As a Source Of Nitrogen Or Electron Acceptormentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Microbial Degradation of 2,4,6-Trinitrotoluene In Vitro and in Natural Environments

Claus

2013

Environmental Science and Engineering

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“…If so, the presence of this ability in indigenous microbial populations could account for the high capacity of TNT degradation in some soils and why field studies with TNT-degrading strain P. putida JLR11 showed little additional effects in the rhizoremediation of TNT-contami- (12). More importantly, if TNT denitration is indeed common in the environment, the recalcitrance and toxicity of diarylamines, as well as its reactivity with organic/inorganic material (7,16), will need to be elucidated. We have found that poorly soluble diarylamines are stable in aqueous solution for months and that these were not further reduced by XenB in vitro.…”

Section: Methyl-35-dinitrophenyl)-4-methyl-35-dinitro-mentioning

confidence: 99%

Type II Hydride Transferases from Different Microorganisms Yield Nitrite and Diarylamines from Polynitroaromatic Compounds

Dillewijn

Wittich

Caballero

et al. 2008

Appl Environ Microbiol

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Homogenous preparations of XenB of Pseudomonas putida, pentaerythritol tetranitrate reductase of Enterobacter cloacae, and N-ethylmaleimide reductase of Escherichia coli, all type II hydride transferases of the Old Yellow Enzyme family of flavoproteins, are shown to reduce the polynitroaromatic compound 2,4,6-trinitrotoluene (TNT). The reduction of this compound yields hydroxylaminodinitrotoluenes and Meisenheimer dihydride complexes, which, upon condensation, yield stoichiometric amounts of nitrite and diarylamines, implying that type II hydride transferases are responsible for TNT denitration, a process with important environmental implications for TNT remediation.Although the polynitroaromatic 2,4,6-trinitrotoluene (TNT) is rather recalcitrant, a number of microorganisms have been described to be able to use this compound as a nitrogen source (reviewed in reference 4). The presence of the three electrophilic nitro substituents on the aromatic ring tends to inactivate its system, thereby preventing oxidative attack by oxygenases that are frequently used by living organisms to catabolize aromatic compounds. Nevertheless, the nitro groups are easily reduced to hydroxylamino groups by nitroreductases (2,8,10,15). Ammonium has been proposed to be released from these derivatives upon a Bamberger-type rearrangement (3,6,8). On the other hand, the aromatic ring of the polynitroaromatic compound is susceptible to nucleophilic attack by hydride ions to form Meisenheimer complex intermediates (13,14). This type of ring reduction is catalyzed by reductases, which are referred to here as type II hydride transferases.Our recent results show that the P. putida XenB protein, a type II hydride transferase of the Old Yellow Enzyme (OYE) family, reduces the nitro groups to produce hydroxylamines and also the aromatic ring to yield the transient production of the Meisenheimer monohydride complex (H Ϫ -TNT), which is further reduced to various isoforms of the Meisenheimer dihydride complex (2H Ϫ -TNT) (19). It is worth noting that nitrite is released in this reaction via the abiotic condensation of enzymatically produced hydroxylaminodinitrotoluenes and Meisenheimer dihydride complexes that yield diarylamines and stoichiometric amounts of nitrite, thereby making a mass balance possible for the first time (19).Several enzymes of the OYE family of flavoproteins (17) with type II hydride transferase activity have been described, i.e., the pentaerythritol tetranitrate (PETN) reductase of Enterobacter cloacae PB2 (5), the N-ethylmaleimide (NEM) reductase of several Escherichia coli strains (6, 18), and xenobiotic reductase B (XenB) of Pseudomonas fluorescens I-C (9). However, the end products formed from TNT by these type II hydride transferases remained unclear, although in the case of the XenB enzyme of P. fluorescens, Pak et al. (9) previously proposed a putative biphenyl structure as an end product based on the molecular mass. A product with a molecular mass similar to that found by Pak et al. (9) was found in cell extracts of E. ...

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“…Mass balance studies indicated the enzyme-catalyzed formation of nonextractable TNT/soil complexes, opening the possibility of soil remediation through cometabolically induced immobilization. Perspectives on the mineralization of polynitroaromatic acids were presented, including the formation of hydride-Meisenheimer complexes of picric acid with reducing equivalents derived from coenzyme F420 (26,43). Nitrite elimination results in the formation of 2,4-dinitrophenol, which can then be further degraded.…”

Section: B3 With Novel Pathways and Enzymes; New Uses For Old Proteinsmentioning

confidence: 99%

Biodegradation, Biotransformation, and Biocatalysis (B3)

Parales

Bruce

Schmid

et al. 2002

Appl Environ Microbiol

102

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Bioelimination of trinitroaromatic compounds: immobilization versus mineralization

Cited by 55 publications

References 28 publications

Microbial Degradation of 2,4,6-Trinitrotoluene In Vitro and in Natural Environments

Microbial Degradation of 2,4,6-Trinitrotoluene In Vitro and in Natural Environments

Type II Hydride Transferases from Different Microorganisms Yield Nitrite and Diarylamines from Polynitroaromatic Compounds

Biodegradation, Biotransformation, and Biocatalysis (B3)

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