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-nitrophenol degradation II
|Superclasses:||Degradation/Utilization/Assimilation → Aromatic Compounds Degradation → Nitroaromatic Compounds Degradation → Nitrophenol Degradation → 4-Nitrophenol Degradation|
|Degradation/Utilization/Assimilation → Aromatic Compounds Degradation → Phenolic Compounds Degradation → Nitrophenol Degradation → 4-Nitrophenol Degradation|
Some taxa known to possess this pathway include : Arthrobacter sp., Lysinibacillus sphaericus, Pseudomonas sp. 1-7, Rhodococcus opacus, Rhodococcus opacus SAO101 [Kitagawa04], Rhodococcus sp. PN1, Serratia sp. DS001, Sphingobium chlorophenolicum, Sphingomonas sp. UG30
Expected Taxonomic Range:
The main input of 4-nitrophenol (p-nitrophenol, PNP) into the environment is the hydrolysis of methyl parathion or parathion, which are commonly used as pesticides in agriculture (see parathion degradation). PNP is also found in industrial wastes since it is a precursor not only of of pesticides such as carbofuran, nitrofen, methyl parathion and parathion, but also of certain pharmaceuticals, plasticizers, azo dyes, explosives etc. In addition, diesel fuel and gasoline exhaust also contain PNP [Tremp93]. Because of the widespread nature of p-nitrophenol and other nitrophenols, they are considered as major pollutants by the United States Environmental Protection Agency (USEPA).
Several bacterial species have the ability to degrade
4-nitrophenol. These include Nocardia
Sphingobium chlorophenolicum and
Sphingomonas sp. UG30
Rhodococcus opacus SAO101
About This Pathway
The key enzyme in this 4-nitrophenol degradation pathway is a two-component hydroxylase that oxidizes PNP to 4-nitrocatechol. The hydroxylase has been detected in several organisms, both Gram-positive and Gram-negative, including Nocardia [Mitra84], Lysinibacillus sphaericus JS905 [Kadiyala98], Rhodococcus sp. PN1 [Takeo03], Rhodococcus opacus SAO101 [Kitagawa04] and Serratia sp. DS001 [Pakala07].
Memebers of this family include two components: an oxygenase, which catalyzes the oxidation of the substrates using reduced flavins, and a reductase whose role is the replenishing of the reduced flavins. A single enzyme from this family catalyzes the first two steps of this pathway [Kadiyala98, Takeo03]. The enzyme generates 1,2,4-benzenetriol and releases stoichiometric amounts of nitrite. 1,2,4-benzenetriol is then oxidized to 2-maleylacetate, which is converted to 3-oxoadipate and shuttled through the 3-oxoadipate degradation pathway to central metabolism.
Variants: 4-nitrophenol degradation I
Relationship Links: Eawag-BBD-Pathways:PART-OF:nphe
Hanne93: Hanne LF, Kirk LL, Appel SM, Narayan AD, Bains KK (1993). "Degradation and induction specificity in actinomycetes that degrade p-nitrophenol." Appl Environ Microbiol 59(10);3505-8. PMID: 8250573
Kadiyala98: Kadiyala V, Spain JC (1998). "A two-component monooxygenase catalyzes both the hydroxylation of p-nitrophenol and the oxidative release of nitrite from 4-nitrocatechol in Bacillus sphaericus JS905." Appl Environ Microbiol 64(7);2479-84. PMID: 9647818
Kitagawa04: Kitagawa W, Kimura N, Kamagata Y (2004). "A novel p-nitrophenol degradation gene cluster from a gram-positive bacterium, Rhodococcus opacus SAO101." J Bacteriol 186(15);4894-902. PMID: 15262926
Pakala07: Pakala SB, Gorla P, Pinjari AB, Krovidi RK, Baru R, Yanamandra M, Merrick M, Siddavattam D (2007). "Biodegradation of methyl parathion and p-nitrophenol: evidence for the presence of a p-nitrophenol 2-hydroxylase in a Gram-negative Serratia sp. strain DS001." Appl Microbiol Biotechnol 73(6);1452-62. PMID: 17043828
Takeo03: Takeo M, Yasukawa T, Abe Y, Niihara S, Maeda Y, Negoro S (2003). "Cloning and characterization of a 4-nitrophenol hydroxylase gene cluster from Rhodococcus sp. PN1." J Biosci Bioeng 95(2);139-45. PMID: 16233382
Tremp93: Tremp, J., Mattrel, P, Fingler, S., Giger, W. (1993). "Phenols and nitrophenols as tropospheric pollutants: emissions from automobile exhausts and phase transfer in the atmosphere." Water Air Soil Poll. 68: 113-123.
Zhang12a: Zhang S, Sun W, Xu L, Zheng X, Chu X, Tian J, Wu N, Fan Y (2012). "Identification of the para-nitrophenol catabolic pathway, and characterization of three enzymes involved in the hydroquinone pathway, in pseudomonas sp. 1-7." BMC Microbiol 12;27. PMID: 22380602
Bondarenko04: Bondarenko S, Gan J, Haver DL, Kabashima JN (2004). "Persistence of selected organophosphate and carbamate insecticides in waters from a coastal watershed." Environ Toxicol Chem 23(11);2649-54. PMID: 15559280
Daubaras96: Daubaras DL, Saido K, Chakrabarty AM (1996). "Purification of hydroxyquinol 1,2-dioxygenase and maleylacetate reductase: the lower pathway of 2,4,5-trichlorophenoxyacetic acid metabolism by Burkholderia cepacia AC1100." Appl Environ Microbiol 62(11);4276-9. PMID: 8900023
Endo05: Endo R, Kamakura M, Miyauchi K, Fukuda M, Ohtsubo Y, Tsuda M, Nagata Y (2005). "Identification and characterization of genes involved in the downstream degradation pathway of gamma-hexachlorocyclohexane in Sphingomonas paucimobilis UT26." J Bacteriol 187(3);847-53. PMID: 15659662
Halak07: Halak S, Basta T, Burger S, Contzen M, Wray V, Pieper DH, Stolz A (2007). "4-sulfomuconolactone hydrolases from Hydrogenophaga intermedia S1 and Agrobacterium radiobacter S2." J Bacteriol 189(19);6998-7006. PMID: 17660282
Kasberg95: Kasberg T, Daubaras DL, Chakrabarty AM, Kinzelt D, Reineke W (1995). "Evidence that operons tcb, tfd, and clc encode maleylacetate reductase, the fourth enzyme of the modified ortho pathway." J Bacteriol 177(13);3885-9. PMID: 7601858
Kasberg97: Kasberg T, Seibert V, Schlomann M, Reineke W (1997). "Cloning, characterization, and sequence analysis of the clcE gene encoding the maleylacetate reductase of Pseudomonas sp. strain B13." J Bacteriol 179(11);3801-3. PMID: 9171435
Kaschabek92: Kaschabek SR, Reineke W (1992). "Maleylacetate reductase of Pseudomonas sp. strain B13: dechlorination of chloromaleylacetates, metabolites in the degradation of chloroaromatic compounds." Arch Microbiol 158(6);412-7. PMID: 1482270
Kaschabek93: Kaschabek SR, Reineke W (1993). "Degradation of chloroaromatics: purification and characterization of maleylacetate reductase from Pseudomonas sp. strain B13." J Bacteriol 175(19);6075-81. PMID: 8407778
Matus03: Matus V, Sanchez MA, Martinez M, Gonzalez B (2003). "Efficient degradation of 2,4,6-Trichlorophenol requires a set of catabolic genes related to tcp genes from Ralstonia eutropha JMP134(pJP4)." Appl Environ Microbiol 69(12);7108-15. PMID: 14660355
Nikodem03: Nikodem P, Hecht V, Schlomann M, Pieper DH (2003). "New bacterial pathway for 4- and 5-chlorosalicylate degradation via 4-chlorocatechol and maleylacetate in Pseudomonas sp. strain MT1." J Bacteriol 185(23);6790-800. PMID: 14617643
Perry07: Perry LL, Zylstra GJ (2007). "Cloning of a gene cluster involved in the catabolism of p-nitrophenol by Arthrobacter sp. strain JS443 and characterization of the p-nitrophenol monooxygenase." J Bacteriol 189(21);7563-72. PMID: 17720792
Seibert93: Seibert V, Stadler-Fritzsche K, Schlomann M (1993). "Purification and characterization of maleylacetate reductase from Alcaligenes eutrophus JMP134(pJP4)." J Bacteriol 175(21);6745-54. PMID: 8226615
Seibert98: Seibert V, Kourbatova EM, Golovleva LA, Schlomann M (1998). "Characterization of the maleylacetate reductase MacA of Rhodococcus opacus 1CP and evidence for the presence of an isofunctional enzyme." J Bacteriol 180(14);3503-8. PMID: 9657989
Shen10: Shen W, Liu W, Zhang J, Tao J, Deng H, Cao H, Cui Z (2010). "Cloning and characterization of a gene cluster involved in the catabolism of p-nitrophenol from Pseudomonas putida DLL-E4." Bioresour Technol 101(19);7516-22. PMID: 20466541
Takenaka03: Takenaka S, Okugawa S, Kadowaki M, Murakami S, Aoki K (2003). "The metabolic pathway of 4-aminophenol in Burkholderia sp. strain AK-5 differs from that of aniline and aniline with C-4 substituents." Appl Environ Microbiol 69(9);5410-3. PMID: 12957929
Takenaka11: Takenaka S, Koshiya J, Okugawa S, Takata A, Murakami S, Aoki K (2011). "Fe-superoxide dismutase and 2-hydroxy-1,4-benzoquinone reductase preclude the auto-oxidation step in 4-aminophenol metabolism by Burkholderia sp. strain AK-5." Biodegradation 22(1);1-11. PMID: 20480210
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