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|
Some taxa known to possess this pathway include : Sphingobium fuliginis
Expected Taxonomic Range: Bacteria
Organophosphate pesticides such as parathion and methyl parathion have been used extensively as insecticides, fungicides, and herbicides. These compounds, being potent cholinesterase inhibitors (see EC 184.108.40.206 and 220.127.116.11 for cholinesterases), are extremely toxic to most animals including humans (in which LD50 is 5 to 10 mg/kg), and may cause death by inducing respiratory failure. Under aerobic conditions, parathion is activated by oxidative desulfuration to the oxygen analog paraoxon [Spencer80], which has a potent anticholinesterase effect and is more toxic than the parent chemical [Guilhermino96].
About This Pathway
The enzymes of the aryldialkylphosphatase family (EC 18.104.22.168) generally have broad substrate specificity, and are capable of accepting many different organophosphate substrates. For more information about this pathway, please see parathion degradation, as the same enzymes catalyze the degradation of paraoxon.
It should be mentioned that the Keasling lab has constructed a genetically engineered Pseudomonas putida strain that can fully mineralize paraoxon [delaPena06]. This organism contains the Sphingobium fuliginis opd gene encoding organophosphate acid anhydrase, the Pseudomonas sp. ENV2030 genes encoding the degradation of 4-nitrophenol (see 4-nitrophenol degradation I), the Delftia acidovorans pdeA gene encoding diethylphosphate phosphodiesterase, and a constitutively expressed phoA gene from Pseudomonas aeruginosa, encoding alkaline phosphatase.
delaPena06: de la Pena Mattozzi M, Tehara SK, Hong T, Keasling JD (2006). "Mineralization of paraoxon and its use as a sole C and P source by a rationally designed catabolic pathway in Pseudomonas putida." Appl Environ Microbiol 72(10);6699-706. PMID: 17021221
Guilhermino96: Guilhermino L, Celeste Lopes M, Carvalho AP, Soares AM (1996). "Inhibition of acetylcholinesterase activity as effect criterion in acute tests with juvenile Daphnia magna." Chemosphere 32(4);727-38. PMID: 8867149
Spencer80: Spencer, W.F., Adams, J.D., Shoup, T.D., Spear, R.C. (1980). "Conversion of Parathion to Paraoxon on Soil Dusts and Clay Minerals as Affected by Ozone and UV Light." J. Agric. Food Chem. 28: 366-371.
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
Harper88: Harper LL, McDaniel CS, Miller CE, Wild JR (1988). "Dissimilar plasmids isolated from Pseudomonas diminuta MG and a Flavobacterium sp. (ATCC 27551) contain identical opd genes." Appl Environ Microbiol 54(10);2586-9. PMID: 3202637
Khajamohiddin06: Khajamohiddin S, Babu PS, Chakka D, Merrick M, Bhaduri A, Sowdhamini R, Siddavattam D (2006). "A novel meta-cleavage product hydrolase from Flavobacterium sp. ATCC27551." Biochem Biophys Res Commun 351(3);675-81. PMID: 17078928
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
Mulbry86: Mulbry WW, Karns JS, Kearney PC, Nelson JO, McDaniel CS, Wild JR (1986). "Identification of a plasmid-borne parathion hydrolase gene from Flavobacterium sp. by southern hybridization with opd from Pseudomonas diminuta." Appl Environ Microbiol 51(5);926-30. PMID: 3015022
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
Siddavattam03: Siddavattam D, Khajamohiddin S, Manavathi B, Pakala SB, Merrick M (2003). "Transposon-like organization of the plasmid-borne organophosphate degradation (opd) gene cluster found in Flavobacterium sp." Appl Environ Microbiol 69(5);2533-9. PMID: 12732518
Zhang09d: Zhang JJ, Liu H, Xiao Y, Zhang XE, Zhou NY (2009). "Identification and characterization of catabolic para-nitrophenol 4-monooxygenase and para-benzoquinone reductase from Pseudomonas sp. strain WBC-3." J Bacteriol 191(8);2703-10. PMID: 19218392
Zhang12c: 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
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