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 → Naphthalene Degradation|
Some taxa known to possess this pathway include : Pseudomonas putida ATCC 17484 , pseudomonas putida NP , Pseudomonas putida PpG7 , Pseudomonas sp. ATCC 17483 , Pseudomonas sp. NCIB9816-4 , Pseudomonas sp. PG , Pseudomonas stutzeri AN10 , Ralstonia sp. U2 , Rhodococcus sp. NCIMB12038
Expected Taxonomic Range: Bacteria
Naphthalene is the simplest fused polycyclic aromatic hydrocarbon, and is abundant in soils. Several bacterial species are able to grow on naphthalene as the sole cource of carbon and energy [Shamsuzzaman74, Bosch99, Kulakov00]. At least two pathways for naphthalene degradation exist - an aerobic pathway and an anaerobic pathway. This pathway describes the aerobic process.
Naphthalene is catabolized through cis naphthalene dihydrodiol, salicylaldehyde, and salicylate. The latter is converted into either catechol, which is then degraded by either the meta or the ortho cleavage pathways to TCA cycle intermediates [Barnsley76], or to gentisate, which is degraded by a different pathway to TCA cycle intermediates [Fuenmayor98] (see salicylate degradation I and salicylate degradation II, respectively).
Several different models have been proposed for this pathway, due to the difficulty working with the unstable intermediate naphthalene-1,2-diol, which is rapidly and spontaneously oxidized in water to 1,2-naphthoquinone. The pathway presented here reflects the results of a careful analysis performed by Eaton and Chapman [Eaton92].
The genes encoding the enzymes required for the catabolism of naphthalene are often carried on plasmids, such as the NAH plasmids [Zakharian, Connors82, Yen82]. However, some organisms, such as Pseudomonas stutzeri AN10, carry these genes on their chromosome [Bosch99]. Transcription of the genes in this operon is regulated by a salicylate-dependent transcription regulator (such as NahR for the operon located on the NAH plasmid) [You86, Schell86].
Variants: naphthalene degradation (anaerobic)
Unification Links: Eawag-BBD-Pathways:naph
Barnsley76: Barnsley EA (1976). "Role and regulation of the ortho and meta pathways of catechol metabolism in pseudomonads metabolizing naphthalene and salicylate." J Bacteriol 125(2);404-8. PMID: 1245462
Bosch99: Bosch R, Garcia-Valdes E, Moore ER (1999). "Genetic characterization and evolutionary implications of a chromosomally encoded naphthalene-degradation upper pathway from Pseudomonas stutzeri AN10." Gene 236(1);149-57. PMID: 10433976
Eaton92: Eaton RW, Chapman PJ (1992). "Bacterial metabolism of naphthalene: construction and use of recombinant bacteria to study ring cleavage of 1,2-dihydroxynaphthalene and subsequent reactions." J Bacteriol 174(23);7542-54. PMID: 1447127
Fuenmayor98: Fuenmayor SL, Wild M, Boyes AL, Williams PA (1998). "A gene cluster encoding steps in conversion of naphthalene to gentisate in Pseudomonas sp. strain U2." J Bacteriol 180(9);2522-30. PMID: 9573207
Kulakov00: Kulakov LA, Allen CC, Lipscomb DA, Larkin MJ (2000). "Cloning and characterization of a novel cis-naphthalene dihydrodiol dehydrogenase gene (narB) from Rhodococcus sp. NCIMB12038." FEMS Microbiol Lett 182(2);327-31. PMID: 10620687
Zakharian: Zakharian RA, Bakunin KA, Gasparian NS, Kocharian ShM, Arakelov GM "[Plasmid characteristics of naphthalene and salicylate biodegradation in Pseudomonas putida]." Mikrobiologiia 49(6);931-5. PMID: 6259498
Beil97: Beil S, Happe B, Timmis KN, Pieper DH (1997). "Genetic and biochemical characterization of the broad spectrum chlorobenzene dioxygenase from Burkholderia sp. strain PS12--dechlorination of 1,2,4,5-tetrachlorobenzene." Eur J Biochem 247(1);190-9. PMID: 9249026
Boronin89: Boronin AM, Tsoi TV, Kosheleva IA, Arinbasarov MU, Adanin VM (1989). "[Cloning of Pseudomonas putida genes responsible for the primary stages of oxidation of naphthalene in Escherichia coli cells]." Genetika 25(2);226-37. PMID: 2661326
Dennis04: Dennis JJ, Zylstra GJ (2004). "Complete sequence and genetic organization of pDTG1, the 83 kilobase naphthalene degradation plasmid from Pseudomonas putida strain NCIB 9816-4." J Mol Biol 341(3);753-68. PMID: 15288784
Gibson95: Gibson DT, Resnick SM, Lee K, Brand JM, Torok DS, Wackett LP, Schocken MJ, Haigler BE (1995). "Desaturation, dioxygenation, and monooxygenation reactions catalyzed by naphthalene dioxygenase from Pseudomonas sp. strain 9816-4." J Bacteriol 177(10);2615-21. PMID: 7751268
Haigler90: Haigler BE, Gibson DT (1990). "Purification and properties of NADH-ferredoxinNAP reductase, a component of naphthalene dioxygenase from Pseudomonas sp. strain NCIB 9816." J Bacteriol 172(1);457-64. PMID: 2294092
Haigler90a: Haigler BE, Gibson DT (1990). "Purification and properties of ferredoxinNAP, a component of naphthalene dioxygenase from Pseudomonas sp. strain NCIB 9816." J Bacteriol 172(1);465-8. PMID: 2294093
Kauppi98: Kauppi B, Lee K, Carredano E, Parales RE, Gibson DT, Eklund H, Ramaswamy S (1998). "Structure of an aromatic-ring-hydroxylating dioxygenase-naphthalene 1,2-dioxygenase." Structure 6(5);571-86. PMID: 9634695
Kurkela88: Kurkela S, Lehvaslaiho H, Palva ET, Teeri TH (1988). "Cloning, nucleotide sequence and characterization of genes encoding naphthalene dioxygenase of Pseudomonas putida strain NCIB9816." Gene 73(2);355-62. PMID: 3243438
Lessner02: Lessner DJ, Johnson GR, Parales RE, Spain JC, Gibson DT (2002). "Molecular characterization and substrate specificity of nitrobenzene dioxygenase from Comamonas sp. strain JS765." Appl Environ Microbiol 68(2);634-41. PMID: 11823201
Parales05: Parales RE, Huang R, Yu CL, Parales JV, Lee FK, Lessner DJ, Ivkovic-Jensen MM, Liu W, Friemann R, Ramaswamy S, Gibson DT (2005). "Purification, characterization, and crystallization of the components of the nitrobenzene and 2-nitrotoluene dioxygenase enzyme systems." Appl Environ Microbiol 71(7);3806-14. PMID: 16000792
Simon93: Simon MJ, Osslund TD, Saunders R, Ensley BD, Suggs S, Harcourt A, Suen WC, Cruden DL, Gibson DT, Zylstra GJ (1993). "Sequences of genes encoding naphthalene dioxygenase in Pseudomonas putida strains G7 and NCIB 9816-4." Gene 127(1);31-7. PMID: 8486285
Thompson07: Thompson LC, Ladner JE, Codreanu SG, Harp J, Gilliland GL, Armstrong RN (2007). "2-Hydroxychromene-2-carboxylic acid isomerase: a kappa class glutathione transferase from Pseudomonas putida." Biochemistry 46(23);6710-22. PMID: 17508726
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