MetaCyc Pathway: nitrobenzene degradation I

Enzyme View:

Pathway diagram: nitrobenzene degradation I

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.

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

Some taxa known to possess this pathway include ? : Comamonas testosteroni CNB-1 , Pseudomonas pseudoalcaligenes JS45 , Pseudomonas putida HS12

Expected Taxonomic Range: Bacteria

Nitrobenzene is frequently released in the effluent from explosives manufacture as well as in the manufacture of organic chemicals and plastics. It is the primary starting material for the manufacture of aniline, a compound used in the production of polyurethane [Nishino93]. The pollution potential of nitrobenzene is very large, and it is listed among the U.S. Environmental Protection Agency priority pollutants [Callahan79].

Pseudomonas pseudoalcaligenes JS45, an isolate from soil and groundwater contaminated with nitrobenzene, is able to use nitrobenzene as the sole source of carbon, nitrogen, and energy. Analysis of cell-free extracts suggested of an initial partial reduction to hydroxyaminobenzene, which undergoes a rearrangement to 2-aminophenol, followed by meta ring cleavage [Nishino93]. Additional work focused on the purification and characterization of all of the key enzymes in the pathway, including nitrobenzene nitroreductase [Somerville95], 2-aminophenol-1,6-dioxygenase [Lendenmann96], 2-aminomuconate deaminase [He98b], 2-aminomucoate semialdehyde dehydrogenase [He98a] and hydroxylaminobenzene mutase [Davis00b] (see 2-aminophenol degradation).

This pathway has also been described in Pseudomonas putida HS12 [Park99]. The portion of the pathway downstream from 2-aminophenol is identical to the 2-aminophenol degradation pathway of Pseudomonas sp. AP3 [Takenaka97, Takenaka98, Takenaka00, Takenaka05].

A different pathway for the degeradation of nitrobenzene is described in nitrobenzene degradation II.

Variants: 4-chloronitrobenzene degradation , nitrobenzene degradation II

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.

Davis00b: Davis JK, Paoli GC, He Z, Nadeau LJ, Somerville CC, Spain JC (2000). "Sequence analysis and initial characterization of two isozymes of hydroxylaminobenzene mutase from Pseudomonas pseudoalcaligenes JS45." Appl Environ Microbiol 66(7);2965-71. PMID: 10877793

He98a: He Z, Davis JK, Spain JC (1998). "Purification, characterization, and sequence analysis of 2-aminomuconic 6-semialdehyde dehydrogenase from Pseudomonas pseudoalcaligenes JS45." J Bacteriol 180(17);4591-5. PMID: 9721300

He98b: He Z, Spain JC (1998). "A novel 2-aminomuconate deaminase in the nitrobenzene degradation pathway of Pseudomonas pseudoalcaligenes JS45." J Bacteriol 180(9);2502-6. PMID: 9573204

Lendenmann96: Lendenmann U, Spain JC (1996). "2-aminophenol 1,6-dioxygenase: a novel aromatic ring cleavage enzyme purified from Pseudomonas pseudoalcaligenes JS45." J Bacteriol 178(21);6227-32. PMID: 8892823

Nishino93: Nishino SF, Spain JC (1993). "Degradation of nitrobenzene by a Pseudomonas pseudoalcaligenes." Appl Environ Microbiol 59(8);2520-5. PMID: 8368838

Park99: Park HS, Lim SJ, Chang YK, Livingston AG, Kim HS (1999). "Degradation of chloronitrobenzenes by a coculture of Pseudomonas putida and a Rhodococcus sp." Appl Environ Microbiol 65(3);1083-91. PMID: 10049867

Somerville95: Somerville CC, Nishino SF, Spain JC (1995). "Purification and characterization of nitrobenzene nitroreductase from Pseudomonas pseudoalcaligenes JS45." J Bacteriol 177(13);3837-42. PMID: 7601851

Takenaka00: Takenaka S, Murakami S, Kim YJ, Aoki K (2000). "Complete nucleotide sequence and functional analysis of the genes for 2-aminophenol metabolism from Pseudomonas sp. AP-3." Arch Microbiol 174(4);265-72. PMID: 11081795

Takenaka05: Takenaka S, Setyorini E, Kim YJ, Murakami S, Aoki K (2005). "Constitutive synthesis of enzymes involved in 2-aminophenol metabolism and inducible synthesis of enzymes involved in benzoate, p-hydroxybenzoate, and protocatechuate metabolism in Pseudomonas sp. strain AP-3." Biosci Biotechnol Biochem 69(5);1033-5. PMID: 15914928

Takenaka97: Takenaka S, Murakami S, Shinke R, Hatakeyama K, Yukawa H, Aoki K (1997). "Novel genes encoding 2-aminophenol 1,6-dioxygenase from Pseudomonas species AP-3 growing on 2-aminophenol and catalytic properties of the purified enzyme." J Biol Chem 272(23);14727-32. PMID: 9169437

Takenaka98: Takenaka S, Murakami S, Shinke R, Aoki K (1998). "Metabolism of 2-aminophenol by Pseudomonas sp. AP-3: modified meta-cleavage pathway." Arch Microbiol 170(2);132-7. PMID: 9683650

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."

Ma07a: Ma YF, Wu JF, Wang SY, Jiang CY, Zhang Y, Qi SW, Liu L, Zhao GP, Liu SJ (2007). "Nucleotide sequence of plasmid pCNB1 from comamonas strain CNB-1 reveals novel genetic organization and evolution for 4-chloronitrobenzene degradation." Appl Environ Microbiol 73(14);4477-83. PMID: 17526790

Wu06: Wu JF, Jiang CY, Wang BJ, Ma YF, Liu ZP, Liu SJ (2006). "Novel partial reductive pathway for 4-chloronitrobenzene and nitrobenzene degradation in Comamonas sp. strain CNB-1." Appl Environ Microbiol 72(3);1759-65. PMID: 16517619

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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