MetaCyc Pathway: 2-nitrophenol degradation
Inferred from experiment

Pathway diagram: 2-nitrophenol 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: ortho-nitrophenol degradation, o-nitrophenol degradation

Superclasses: Degradation/Utilization/AssimilationAromatic Compounds DegradationNitroaromatic Compounds DegradationNitrophenol Degradation2-Nitrophenol Degradation
Degradation/Utilization/AssimilationAromatic Compounds DegradationPhenolic Compounds DegradationNitrophenol Degradation2-Nitrophenol Degradation

Some taxa known to possess this pathway include : Pseudomonas putida B2

Expected Taxonomic Range: Bacteria

Nitroaromatic compounds are found in many pesticides, dyes, explosives, and solvents, and they also serve as precursors for the production of aminoaromatic derivatives. Because of their common usage, nitroaromatic compounds have become pollutants in rivers, wastewaters, groundwaters, pesticide-treated soils, and the atmosphere. 2-nitrophenol (ONP) and 2,4-dinitrophenol have been listed as priority pollutants by the U.S. Environmental Protection Agency [Callahan79].

Degradation of 2-nitrophenol by Pseudomonas has been reported several times in the literature [Simpson53, Germanier63]. A Pseudomonas putida strain that grew on 2-nitrophenol and m-nitrophenol as sole sources of carbon and nitrogen was isolated from soil by Zeyer and Kearney [Zeyer84]. Growing and resting cells degraded 2-nitrophenol and released nitrite. Experiments with a cell-free system demonstrated that the organism possessed an inducible enzyme that degraded 2-nitrophenol to nitrite and catechol [Zeyer84]. The later was further degraded via 3-oxoadipate by the ortho-cleavage system (see catechol degradation III (ortho-cleavage pathway) [Zeyer86].

The responsible enzyme, 2-nitrophenol 2-monooxygenase, has been purified and characterized [Zeyer88].

Relationship Links: Eawag-BBD-Pathways:PART-OF:nphe

Created 23-Aug-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.

Germanier63: Germanier, R., Wuhrmann, K. (1963). "[On aerobic microbial reduction of aromatic nitro compounds]." Pathol Microbiol (Basel) 26;569-78. PMID: 14114131

Simpson53: Simpson, J.R., Evans, W.C. (1953). "The metabolism of nitrophenols by certain bacteria." Biochem J 55(320th Meeting);xxiv. PMID: 13093710

Zeyer84: Zeyer, J., Kearney, P. C. (1984). "Degradation of o-Nitrophenol and m-Nitrophenol by a Pseudomonas putida." J. Agric. Food Chem. 32: 238-242.

Zeyer86: Zeyer J, Kocher HP, Timmis KN (1986). "Influence of para-substituents on the oxidative metabolism of o-nitrophenols by Pseudomonas putida B2." Appl Environ Microbiol 52(2);334-9. PMID: 3752997

Zeyer88: Zeyer J, Kocher HP (1988). "Purification and characterization of a bacterial nitrophenol oxygenase which converts ortho-nitrophenol to catechol and nitrite." J Bacteriol 170(4);1789-94. PMID: 3350791

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

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

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 Nov 28, 2015, BIOCYC13A.