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1.3.1.58

Accepted name:

2,3-dihydroxy-2,3-dihydro-p-cumate dehydrogenase

Reaction:

cis-5,6-dihydroxy-4-isopropylcyclohexa-1,3-dienecarboxylate + NAD⁺ = 2,3-dihydroxy-p-cumate + NADH + H⁺

For diagram of reaction, click here

Glossary:

p-cumic acid = 4-isopropylbenzoic acid
p-cymene = 1-methyl-4-isopropylbenzene

Systematic name:

cis-2,3-dihydroxy-2,3-dihydro-p-cumate:NAD⁺ oxidoreductase

Comments:

Involved in the p-cymene degradation pathway in Pseudomonas putida.

Links to other databases:

BRENDA, EAWAG-BBD, EXPASY, KEGG, MetaCyc, CAS registry number: 176591-33-6

References:

1.	Eaton, R.W. p-Cumate catabolic pathway in Pseudomonas putida Fl: cloning and characterization of DNA carrying the cmt operon. J. Bacteriol. 178 (1996) 1351–1362. [DOI] [PMID: 8631713]

[EC 1.3.1.58 created 2000]

1.14.12.25

Accepted name:

p-cumate 2,3-dioxygenase

Reaction:

p-cumate + NADH + H⁺ + O₂ = (2R,3S)-2,3-dihydroxy-2,3-dihydro-p-cumate + NAD⁺

For diagram of EC 1.14.12, click here

Glossary:

p-cumate = 4-isopropylbenzoate
(2R,3S)-2,3-dihydroxy-2,3-dihydro-p-cumate = (5S,6R)-5,6-dihydroxy-4-isopropylcyclohexa-1,3-diene-1-carboxylate

Systematic name:

4-isopropylbenzoate:oxygen 2,3-oxidoreductase

Comments:

The enzyme, characterized from several Pseudomonas strains, is involved in the degradation of p-cymene and p-cumate. It comprises four components: a ferredoxin, a ferredoxin reductase, and two subunits of a catalytic component. The enzyme can also act on indole, transforming it to the water-insoluble blue dye indigo.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc

References:

1.	DeFrank, J.J. and Ribbons, D.W. p-cymene pathway in Pseudomonas putida: initial reactions. J. Bacteriol. 129 (1977) 1356–1364. [PMID: 845117]
2.	Wigmore, G.J. and Ribbons, D.W. p-Cymene pathway in Pseudomonas putida: selective enrichment of defective mutants by using halogenated substrate analogs. J. Bacteriol. 143 (1980) 816–824. [PMID: 7204334]
3.	Eaton, R.W. and Chapman, P.J. Formation of indigo and related compounds from indolecarboxylic acids by aromatic acid-degrading bacteria: chromogenic reactions for cloning genes encoding dioxygenases that act on aromatic acids. J. Bacteriol. 177 (1995) 6983–6988. [DOI] [PMID: 7592495]
4.	Eaton, R.W. p-Cumate catabolic pathway in Pseudomonas putida Fl: cloning and characterization of DNA carrying the cmt operon. J. Bacteriol. 178 (1996) 1351–1362. [DOI] [PMID: 8631713]

[EC 1.14.12.25 created 2016]

1.14.15.25

Accepted name:

p-cymene methyl-monooxygenase

Reaction:

p-cymene + O₂ + 2 reduced ferredoxin [iron-sulfur] cluster + 2 H⁺ = 4-isopropylbenzyl alcohol + 2 oxidized ferredoxin [iron-sulfur] cluster + H₂O

Glossary:

p-cymene = 4-methyl-1-(propan-2-yl)benzene

Other name(s):

cymAa (gene name); cymA (gene name); p-cymene methyl hydroxylase

Systematic name:

p-cymene,ferredoxin:oxygen oxidoreductase (methyl-hydroxylating)

Comments:

The enzyme, characterized from several Pseudomonas strains, initiates p-cymene catabolism through hydroxylation of the methyl group. The enzyme has a distinct preference for substrates containing at least an alkyl or heteroatom substituent at the para-position of toluene. The electrons are provided by a reductase (EC 1.18.1.3, ferredoxin—NAD⁺ reductase) that transfers electrons from NADH via FAD and an [2Fe-2S] cluster. In Pseudomonas chlororaphis the presence of a third component of unknown function greatly increases the activity. cf. EC 1.14.15.26, toluene methyl-monooxygenase.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc

References:

1.	Eaton, R.W. p-Cymene catabolic pathway in Pseudomonas putida F1: cloning and characterization of DNA encoding conversion of p-cymene to p-cumate. J. Bacteriol. 179 (1997) 3171–3180. [DOI] [PMID: 9150211]
2.	Dutta, T.K. and Gunsalus, I.C. Reductase gene sequences and protein structures: p-cymene methyl hydroxylase. Biochem. Biophys. Res. Commun. 233 (1997) 502–506. [DOI] [PMID: 9144566]
3.	Nishio, T., Patel, A., Wang, Y. and Lau, P.C. Biotransformations catalyzed by cloned p-cymene monooxygenase from Pseudomonas putida F1. Appl. Microbiol. Biotechnol. 55 (2001) 321–325. [PMID: 11341314]
4.	Dutta, T.K., Chakraborty, J., Roy, M., Ghosal, D., Khara, P. and Gunsalus, I.C. Cloning and characterization of a p-cymene monooxygenase from Pseudomonas chlororaphis subsp. aureofaciens. Res. Microbiol. 161 (2010) 876–882. [DOI] [PMID: 21035544]

[EC 1.14.15.25 created 2018]