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MetaCyc Pathway: 4-nitrobenzoate degradation
Inferred from experiment

Enzyme View:

Pathway diagram: 4-nitrobenzoate degradation

This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Synonyms: p-nitrobenzoate degradation

Superclasses: Degradation/Utilization/AssimilationAromatic Compounds DegradationNitroaromatic Compounds DegradationNitrobenzoate Degradation

Some taxa known to possess this pathway include : Delftia acidovorans, Pseudomonas putida TW3, Pseudomonas sp. NT4, Ralstonia pickettii

Expected Taxonomic Range: Proteobacteria

General Background

Nitroaromatic compounds such as nitrophenols, nitrotoluenes and nitrobenzoates, are used in the synthesis of pesticides, plasticizers, dyes, pharmaceuticals, and explosives. These compounds are contaminants of waste waters, rivers and groundwater, and of the atmosphere [Leuenberger88]. In most cases nitroaromatic compounds are highly toxic to living organisms, and several of them have been listed as priority pollutants by the U.S. Environmental Protection Agency [Callahan79].

Despite their toxicity, these compounds can be degraded by several microorganisms. These degradation pathways almost always start with the removal or replacement of the nitro group [MarvinSikkema94]. The mechanisms in which bacteria are able to remove the nitro group can be divided into two broad categories - oxidative and reductive. In oxidative pathways the nitro group is released in the form of nitrite, usually catalyzed by a mono- or di-oxygenase enzymes. For examples, see 2-nitrotoluene degradation and 4-Nitrotoluene Degradation. In reductive pathways the nitro group is reduced via a nitroso intermediate to a hydroxylamino group, and sometime further to an amino group, and is released in the form of ammonia. For examples see 4-nitrotoluene degradation II and 4-nitrobenzoate degradation.

About This Pathway

Several bacterial strains are capable of utilizing 4-nitrobenzoate as the sole source of carbon and energy. The degradation of 4-nitrobenzoate was first demonstrated for a Delftia acidovorans strain [Groenewegen92]. This process proceeds through partial reduction of the nitro group prior to its release as ammonia.

The first enzyme of this pathway, 4-nitrobenzoate reductase, catalyzes the transformation of 4-nitrobenzoate to 4-hydroxylaminobenzoate. The hydroxylamino group is subsequently removed from the aromatic ring as ammonia through the action of a 4-hydroxylaminobenzoate lyase with the concomitant formation of protocatechuate. This reductive pathway for 4-nitrobenzoate degradation has also been shown in Ralstonia pickettii [Yabannavar95] and in several strains of Pseudomonas putida which degrade 4-nitrotoluene [RhysWilliams93, Haigler93].

The genes encoding the enzymes of this pathway, pnbA and pnbB, have been cloned and sequenced from Pseudomonas putida TW3 and from Ralstonia pickettii.

Created 03-Dec-2004 by Caspi R, SRI International
Revised 10-Sep-2007 by Caspi R, SRI International


Callahan79: Callahan, M. A., Slimak, M. W., Gabel, N. W., May, J. P., Fowler, C. F., Freed, J. R., Jennings, P., Durfee, R. L., Whitmore, F. C., Maestri, B., Mabey, W. R., Holt, B. R., Gould, C. (1979). "Water-related environmental fate of 129 priority pollutants." EPA report-440/4-79-029b. U.S. Environmental Protection Agency, Washington, D.C.

Groenewegen92: Groenewegen PE, Breeuwer P, van Helvoort JM, Langenhoff AA, de Vries FP, de Bont JA (1992). "Novel degradative pathway of 4-nitrobenzoate in Comamonas acidovorans NBA-10." J Gen Microbiol 138 ( Pt 8);1599-605. PMID: 1527502

Haigler93: Haigler BE, Spain JC (1993). "Biodegradation of 4-nitrotoluene by Pseudomonas sp. strain 4NT." Appl Environ Microbiol 59(7);2239-43. PMID: 8357257

Leuenberger88: Leuenberger, C., Czuczwa, J., Tremp, J., Giger, W. (1988). "Nitrated phenols in rain: Atmospheric occurrence of phytotoxic pollutants." Chemosphere 17(3): 511-515.

MarvinSikkema94: Marvin-Sikkema FD, de Bont JA (1994). "Degradation of nitroaromatic compounds by microorganisms." Appl Microbiol Biotechnol 42(4);499-507. PMID: 7765729

RhysWilliams93: Rhys-Williams W, Taylor SC, Williams PA (1993). "A novel pathway for the catabolism of 4-nitrotoluene by Pseudomonas." J Gen Microbiol 1993;139 ( Pt 9);1967-72. PMID: 8245826

Yabannavar95: Yabannavar AV, Zylstra GJ (1995). "Cloning and characterization of the genes for p-nitrobenzoate degradation from Pseudomonas pickettii YH105." Appl Environ Microbiol 61(12);4284-90. PMID: 8534095

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

Hughes01: Hughes MA, Williams PA (2001). "Cloning and characterization of the pnb genes, encoding enzymes for 4-nitrobenzoate catabolism in Pseudomonas putida TW3." J Bacteriol 2001;183(4);1225-32. PMID: 11157934

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

Lim02: Lim EK, Doucet CJ, Li Y, Elias L, Worrall D, Spencer SP, Ross J, Bowles DJ (2002). "The activity of Arabidopsis glycosyltransferases toward salicylic acid, 4-hydroxybenzoic acid, and other benzoates." J Biol Chem 277(1);586-92. PMID: 11641410

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 19.5 on Sat Apr 30, 2016, BIOCYC11A.