superpathway of aerobic toluene degradation
Marín M, Plumeier I, Pieper DH. Degradation of 2,3-dihydroxybenzoate by a novel meta-cleavage pathway. J Bacteriol. 2012 Aug;194(15):3851–60. PMID: 22609919; PMCID: PMC3416551.; Johnson DR, Park J, Kukor JJ, Abriola LM. Effect of carbon starvation on toluene degradation activity by toluene monooxygenase-expressing bacteria. Biodegradation. 2006 Oct;17(5):437–45. doi: 10.1007/s10532-005-9014-x. PMID: 16477358.; Fishman A, Tao Y, Wood TK. Toluene 3-Monooxygenase of Ralstonia pickettii PKO1 Is a para -Hydroxylating Enzyme. J Bacteriol. 2004 May 15;186(10):3117–23. doi: 10.1128/jb.186.10.3117-3123.2004.; Newman LM, Wackett LP. Purification and characterization of toluene 2-monooxygenase from Burkholderia cepacia G4. Biochemistry. 1995 Oct 31;34(43):14066–76. doi: 10.1021/bi00043a012. PMID: 7578004.; Inoue J, Shaw JP, Rekik M, Harayama S. Overlapping substrate specificities of benzaldehyde dehydrogenase (the xylC gene product) and 2-hydroxymuconic semialdehyde dehydrogenase (the xylG gene product) encoded by TOL plasmid pWW0 of Pseudomonas putida. J Bacteriol. 1995 Mar;177(5):1196–201. doi: 10.1128/jb.177.5.1196-1201.1995.; Olsen RH, Kukor JJ, Kaphammer B. A novel toluene-3-monooxygenase pathway cloned from Pseudomonas pickettii PKO1. J Bacteriol. 1994 Jun;176(12):3749–56. doi: 10.1128/jb.176.12.3749-3756.1994.; Shaw JP, Rekik M, Schwager F, Harayama S. Kinetic studies on benzyl alcohol dehydrogenase encoded by TOL plasmid pWWO. A member of the zinc-containing long chain alcohol dehydrogenase family. Journal of Biological Chemistry. 1993 May;268(15):10842–50. doi: 10.1016/s0021-9258(18)82062-2.; Yen KM, Karl MR, Blatt LM, Simon MJ, Winter RB, Fausset PR, Lu HS, Harcourt AA, Chen KK. Cloning and characterization of a Pseudomonas mendocina KR1 gene cluster encoding toluene-4-monooxygenase. J Bacteriol. 1991 Sep;173(17):5315–27. doi: 10.1128/jb.173.17.5315-5327.1991.; Kukor JJ, Olsen RH. Genetic organization and regulation of a meta cleavage pathway for catechols produced from catabolism of toluene, benzene, phenol, and cresols by Pseudomonas pickettii PKO1. J Bacteriol. 1991 Aug;173(15):4587–94. doi: 10.1128/jb.173.15.4587-4594.1991.; Menn FM, Zylstra GJ, Gibson DT. Location and sequence of the todF gene encoding 2-hydroxy-6-oxohepta-2,4-dienoate hydrolase in Pseudomonas putida F1. Gene. 1991 Jul 31;104(1):91–4. doi: 10.1016/0378-1119(91)90470-v. PMID: 1916282.
Metabolites
Enzyme
| EC Number | name | full name | note |
|---|---|---|---|
| 1.13.11.- | |||
| 1.1.1.90 | aryl-alcohol dehydrogenase | aryl-alcohol:NAD+ oxidoreductase | |
| 1.13.11.2 | catechol 2,3-dioxygenase | catechol:oxygen 2,3-oxidoreductase (decyclizing) | |
| 1.14.13.236 | toluene 4-monooxygenase | toluene,NADH:oxygen oxidoreductase (4-hydroxylating) | |
| 1.14.15.26 | toluene methyl-monooxygenase | methylbenzene,ferredoxin:oxygen oxidoreductase (methyl-hydroxylating) | |
| 1.18.1.3 | ferredoxin-NAD+ reductase | ferredoxin:NAD+ oxidoreductase | |
| 1.2.1.28 | benzaldehyde dehydrogenase (NAD+) | benzaldehyde:NAD+ oxidoreductase | |
| 1.2.1.85 | 2-hydroxymuconate-6-semialdehyde dehydrogenase | 2-hydroxymuconate-6-semialdehyde:NAD+ oxidoreductase | |
| 1.3.1.25 | 1,6-dihydroxycyclohexa-2,4-diene-1-carboxylate dehydrogenase | (1R,6S)-1,6-dihydroxycyclohexa-2,4-diene-1-carboxylate:NAD+ oxidoreductase (decarboxylating) | |
| 3.7.1.25 | 2-hydroxy-6-oxohepta-2,4-dienoate hydrolase | (2Z,4E)-2-hydroxy-6-oxohepta-2,4-dienoate acetylhydrolase | |
| 3.7.1.9 | 2-hydroxymuconate-6-semialdehyde hydrolase | 2-hydroxymuconate-6-semialdehyde formylhydrolase | |
| 4.1.1.77 | 2-oxo-3-hexenedioate decarboxylase | (3E)-2-oxohex-3-enedioate carboxy-lyase (2-oxopent-4-enoate-forming) | |
| 4.1.3.39 | 4-hydroxy-2-oxovalerate aldolase | 4-hydroxy-2-oxopentanoate pyruvate-lyase (acetaldehyde-forming) | |
| 5.3.2.6 | 2-hydroxymuconate tautomerase | (2Z,4E)-2-hydroxyhexa-2,4-dienedioate keto-enol isomerase |
Proteins
| Protein ID | name | full name |
|---|---|---|
| A5W4E9 | todA | Toluene 1,2-dioxygenase system ferredoxin--NAD(+) reductase component |
| P06622 | xylE | Metapyrocatechase |
| P13453 | todE | 3-methylcatechol 2,3-dioxygenase |
| P13859 | todD | Cis-toluene dihydrodiol dehydrogenase |
| P21395 | xylM | Xylene/toluene monooxygenase hydroxylase component XylM |
| P23099 | xylX | Toluate 1,2-dioxygenase subunit alpha |
| P23100 | xylY | Toluate 1,2-dioxygenase subunit beta |
| P23101 | xylZ | Toluate 1,2-dioxygenase electron transfer component |
| P23102 | xylL | 1,6-dihydroxycyclohexa-2,4-diene-1-carboxylate dehydrogenase |
| P23105 | xylG | 2-hydroxymuconic semialdehyde dehydrogenase |
| P23106 | xylF | 2-hydroxymuconate semialdehyde hydrolase |
| P23107 | xylJ | 2-hydroxypent-2,4-dienoate hydratase |
| P23133 | todF | 2-hydroxy-6-oxo-2,4-heptadienoate hydrolase |
| P39849 | xylB | Aryl-alcohol dehydrogenase |
| P43503 | xylC | Benzaldehyde dehydrogenase [NAD(+)] |
| P49155 | xylI | 4-oxalocrotonate decarboxylase |
| P51018 | todH | 4-hydroxy-2-oxovalerate aldolase 1 |
| Q00456 | tmoA | Toluene-4-monooxygenase system, hydroxylase component subunit alpha |
| Q00457 | tmoB | Toluene-4-monooxygenase system, hydroxylase component subunit gamma |
| Q00460 | tmoE | Toluene-4-monooxygenase system, hydroxylase component subunit beta |
| Q01468 | xylH | 2-hydroxymuconate tautomerase |
| Q03304 | tmoF | Toluene-4-monooxygenase system, ferredoxin--NAD(+) reductase component |