Covalent Binding of Reduced Metabolites of [15N3]TNT to Soil Organic Matter during a Bioremediation Process Analyzed by 15N NMR Spectroscopy

Achtnich, Christof; Fernandes, Errol; Bollag, Jean‐Marc; Knackmuss, Hans‐Joachim; Lenke, Hiltrud

doi:10.1021/es990427+

Cited by 89 publications

(86 citation statements)

References 25 publications

(68 reference statements)

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“…Most contamination is limited to manufacture and disposal sites, but it is still problematic, since TNT persists in the environment for long periods, is acutely toxic, and is readily transformed into carcinogenic compounds (13). Current strategies for remediation of TNT-contaminated soil involve a number of practices, including chemical treatment, physical processes, land farming, phytoremediation, and other combined biological processes (1,16,31). However, no current treatment short of incineration is widely used for complete detoxification and mineralization of TNT.…”

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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“…Absorption into natural organic matter (NOM) has been identified as a significant process for organic contaminants in environments where NOM is greater than >0.2% , which would be expected in estuarine systems. Many of these terrestrial and groundwater studies identify the association of TNT and particulate organic matter (POM) as an irreversible binding (Selim et al 1995, Comfort et al 1995, Pennington et al 1995, Achtnich et al 1999, Pennington et al 1990) but in the presence of live bacterial assemblages, it would be difficult to differentiate radiolabel incorporated into bacterial macromolecules from covalent binding to POM. The presence of colloidal and dissolved organic matter (DOM), may also impact the fate of TNT in the marine water column and sedimentary porewater, as indicated in previous investigations on the enhanced water solubility of several organic pollutants by dissolved humic and fulvic acids (Chiou et al 1986).…”

Section: Abiotic -Chemicalmentioning

confidence: 99%

Mineralization of 2,4,6-Trinitrotoleune (TNT) in Coastal Waters and Sediments

Walker¹,

Osburn²,

Boyd³

et al. 2006

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Standard Form 298 (Rev. 8-98)Prescribed by ANSI Std. Z39.18Public reporting burden for this 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 this collection of information. Approved for public release; distribution is unlimited. PERFORMING ORGANIZATION NAME(S) AND ADDRESS(ES) SPONSOR / MONITOR'S ACRONYM(S) 9. SPONSORING / MONITORING AGENCY NAME(S) AND ADDRESS(ES)11 Unclassified Unclassified UnclassifiedUnlimited 42Michael T. Montgomery 202-404-6419Mineralization rates of 14C-TNT, -DNT, and -DAT were measured in surface sediments, with depth in sediment cores, and in the water column during 12 research cruises over the past 4 years in the San Francisco Bay, Chesapeake Bay, and Hawaii. Mineralization rates were also compared to uptake and incorporation rates of TNT, DNT, and DAT into the natural microbial assemblage. In general, the bacterial mineralizations rates were similar, or an order of magnitude faster, than those for organic hydrocarbons measured at the same time. Using seawater sampled from a historical UXO field, we found that while bacterial mineralization was rapid (>1 ug L-1 d-1, unfiltered water in dark), photodegradation was even faster (16 ug L-1 d-1, filtered water in light) and the combination of light and unfiltered water was greater than the sum of the two rates (103 ug L-1 d-1), suggesting either that the prescnce of active phytoplankton is important or photodegradation enhances bacterial mineralization.

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“…Others have hypothesized that the bioavailability of TNT and related NACs in soil is dependent upon the OM content (Achtnich et al, 1999;Anzhi et al, 1997;Eriksson and Skyllberg, 2001;Simpson, 2006;Thorn and Kennedy, 2002), or the clay content (Emery et al, 2001;Haderlein et al, 1996), or a combination of the two (Jaenig, 2006). The WCL soil, which had the greatest percentages of both OM (5.3%) and clay (28%) among the five soil types in the present studies, produced the least resulting toxicities for all three plant species exposed.…”

Section: Discussionmentioning

confidence: 99%

Toxicities of TNT and RDX to Terrestrial Plants in Five Soils with Contrasting Characteristics

Simini¹,

Checkai²,

Phillips³

et al. 2013

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Public reporting burden for this 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 this 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 Department of Defense, Washington Headquarters Services, Directorate for Information Operations and Reports (0704-0188), 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 any penalty for failing to comply with a collection of information if it does not display a currently valid OMB control number. PLEASE DO NOT RETURN YOUR FORM TO THE ABOVE ADDRESS. REPORT DATE (DD-MM-YYYY)XX-07-2013 REPORT TYPE AUTHOR(S)Simini, Michael; Checkai, Ronald T.; Kuperman, Roman G.; Phillips, Carlton T.; Kolakowski, Jan E.; and Kurnas, Carl W. PERFORMING ORGANIZATION NAME(S) AND ADDRESS(ES)Director, ECBC, ATTN: RDCB-DRT-E, APG, MD 21010-5424 PERFORMING ORGANIZATION REPORT NUMBER ECBC-TR-1091 SPONSORING / MONITORING AGENCY NAME(S) AND ADDRESS(ES)Strategic Environmental Research and Development Program 4800 Mark Center Drive, Suite 17D08, Alexandria, VA 22350-3605 SPONSOR/MONITOR'S ACRONYM(S) SERDP SPONSOR/MONITOR'S REPORT NUMBER(S) DISTRIBUTION / AVAILABILITY STATEMENTApproved for public release; distribution is unlimited. SUPPLEMENTARY NOTES ABSTRACT-LIMIT 200 WORDSThis study was designed to produce scientifically defensible benchmark data for the development of ecological-based soil screening levels for 2,4,6-trinitrotoluene (TNT) and hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) for terrestrial plants. The physical and chemical properties of different soils may alter the bioavailability and toxicity of TNT and RDX to plant species. We investigated individual ecotoxicities of TNT and RDX to alfalfa (Medicago sativa L.), Japanese millet (J. millet; Echinochloa crus-galli L. [Beauv.]), and perennial ryegrass (Lolium perenne L.) in five natural soils that varied in pH, organic matter, and clay contents. On the basis of EC 50 values (the TNT or RDX concentrations that produce 50% reductions in selected measurement endpoints) and 95% confidence intervals for shoot fresh and dry masses (SDM), TNT weathered-and-aged (W-A) in soils significantly reduced (p < 0.05) growth of alfalfa, J. millet, and perennial ryegrass. RDX W-A in soil was moderately inhibitory to growth of J. millet and perennial ryegrass in all five soils but did not affect growth of alfalfa. No statistically significant correlations between TNT toxicity and these soil properties were identified; however, statistically significant (p < 0.05) inverse relationships were identified between the RDX EC 50 values for perennial ryegrass SDM and soil clay content and pH.

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Covalent Binding of Reduced Metabolites of [¹⁵N₃]TNT to Soil Organic Matter during a Bioremediation Process Analyzed by ¹⁵N NMR Spectroscopy

Cited by 89 publications

References 25 publications

Oxidative Transformation of Aminodinitrotoluene Isomers by Multicomponent Dioxygenases

Oxidative Transformation of Aminodinitrotoluene Isomers by Multicomponent Dioxygenases

Mineralization of 2,4,6-Trinitrotoleune (TNT) in Coastal Waters and Sediments

Toxicities of TNT and RDX to Terrestrial Plants in Five Soils with Contrasting Characteristics

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