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MetaCyc Pathway: 2,4,6-trinitrotoluene degradation

If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Synonyms: TNT degradation

Superclasses: Degradation/Utilization/Assimilation Aromatic Compounds Degradation Nitroaromatic Compounds Degradation Nitrotoluene Degradation

Some taxa known to possess this pathway include ? : Arabidopsis thaliana col

Expected Taxonomic Range: Viridiplantae

Summary:
2,4,6-Trinitrotoluene (TNT), a nitroaromatic explosive, is a highly persistent organic pollutant introduced into the environment from the industries involved in the manufacture, packaging, use and decommissioning of explosives. It is a primary target for remediation because of its toxicity (as a class-C carcinogen) and the global extent of environmental contamination.

Phytoremidiation is emerging as a viable alternative strategy to the current methods of TNT clean-up. With their extensive root systems, plants have a remarkable ability to extract compounds from their surroundings.Several studies have investigated the tolerance of plants to TNT and the active uptake of TNT by plant roots. a study with the aquatic plant Myriophyllum spicatum (Eurasian Watermilfoil) has shown that it can transforms TNT. Rapid disappearance of TNT from the plant culture media was followed by the appearance of aminodinitrotoluenes (ADNT), with lower levels of hydroxylaminodinitrotoluene (HADNT) and diaminonitrotoluenes (DANT). However, these products accounted for less than 20% of the transformed TNT. The unaccounted for mass of TNT and/or transformation products was not detectable in the plant culture media nor was it extractable from the plant matrix [Pavlostathis98].

A later study with Arabidopsis thaliana has demonstrated the reductive transformation of TNT to hydroxylaminodinitrotoluene (HADNT), and then aminodinitrotoluene (ADNT), followed by glucosylation [GandiaHerrero08].

Credits:
Created 24-Sep-2008 by Karthikeyan AS , TAIR


References

GandiaHerrero08: Gandia-Herrero F, Lorenz A, Larson T, Graham IA, Bowles DJ, Rylott EL, Bruce NC (2008). "Detoxification of the explosive 2,4,6-trinitrotoluene in Arabidopsis- discovery of bifunctional O- and C-glucosyltransferases." Plant J NIL. PMID: 18702669

Pavlostathis98: Pavlostathis, S.G., Comstock, K.K., Jacobson, M.E., Sauders, F.M. (1998). "Transformation of 2,4,6-trinitrotolueneby the aquatic plant Myriophyllum spicatum. Environ." Environ. Toxicol. Chem. 17, 2266-2273.

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

Hou04: Hou B, Lim EK, Higgins GS, Bowles DJ (2004). "N-glucosylation of cytokinins by glycosyltransferases of Arabidopsis thaliana." J Biol Chem 279(46);47822-32. PMID: 15342621

Jones03: Jones P, Messner B, Nakajima J, Schaffner AR, Saito K (2003). "UGT73C6 and UGT78D1, glycosyltransferases involved in flavonol glycoside biosynthesis in Arabidopsis thaliana." J Biol Chem 278(45);43910-8. PMID: 12900416

Kim06f: Kim JH, Kim BG, Ko JH, Lee Y, Hur H-G, Lim Y, Ahn J-H (2006). "Molecular cloning, expression, and characterization of a flavonoid glycosyltransferase from Arabidopsis thaliana." Plant Science, 170(4), 897-903.

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Lazarowski03: Lazarowski ER, Shea DA, Boucher RC, Harden TK (2003). "Release of cellular UDP-glucose as a potential extracellular signaling molecule." Mol Pharmacol 63(5);1190-7. PMID: 12695547

Martin01: Martin RC, Mok MC, Habben JE, Mok DW (2001). "A maize cytokinin gene encoding an O-glucosyltransferase specific to cis-zeatin." Proc Natl Acad Sci U S A 98(10);5922-6. PMID: 11331778

Tognetti10: Tognetti VB, Van Aken O, Morreel K, Vandenbroucke K, van de Cotte B, De Clercq I, Chiwocha S, Fenske R, Prinsen E, Boerjan W, Genty B, Stubbs KA, Inze D, Van Breusegem F (2010). "Perturbation of Indole-3-Butyric Acid Homeostasis by the UDP-Glucosyltransferase UGT74E2 Modulates Arabidopsis Architecture and Water Stress Tolerance." Plant Cell. PMID: 20798329

Veach03: Veach YK, Martin RC, Mok DW, Malbeck J, Vankova R, Mok MC (2003). "O-glucosylation of cis-zeatin in maize. Characterization of genes, enzymes, and endogenous cytokinins." Plant Physiol 131(3);1374-80. PMID: 12644686

Willits04: Willits MG, Giovanni M, Prata RT, Kramer CM, De Luca V, Steffens JC, Graser G (2004). "Bio-fermentation of modified flavonoids: an example of in vivo diversification of secondary metabolites." Phytochemistry 65(1);31-41. PMID: 14697269


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Sun Nov 23, 2014, BIOCYC13B.