KEGG   ENZYME: 1.14.15.25
Entry
EC 1.14.15.25               Enzyme                                 
Name
p-cymene methyl-monooxygenase;
cymAa (gene name);
cymA (gene name);
p-cymene methyl hydroxylase
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With reduced iron-sulfur protein as one donor, and incorporation of one atom of oxygen into the other donor
Sysname
p-cymene,ferredoxin:oxygen oxidoreductase (methyl-hydroxylating)
Reaction(IUBMB)
p-cymene + O2 + 2 reduced ferredoxin [iron-sulfur] cluster + 2 H+ = 4-isopropylbenzyl alcohol + 2 oxidized ferredoxin [iron-sulfur] cluster + H2O [RN:R05266]
Reaction(KEGG)
R05266
Substrate
p-cymene [CPD:C06575];
O2 [CPD:C00007];
reduced ferredoxin [iron-sulfur] cluster [CPD:C00138];
H+ [CPD:C00080]
Product
4-isopropylbenzyl alcohol [CPD:C06576];
oxidized ferredoxin [iron-sulfur] cluster [CPD:C00139];
H2O [CPD:C00001]
Comment
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.
History
EC 1.14.15.25 created 2018
Pathway
ec00622  Xylene degradation
ec01100  Metabolic pathways
ec01120  Microbial metabolism in diverse environments
Orthology
K10616  p-cymene methyl-monooxygenase
Genes
PPFPput_2903
PPXT1E_4243(xylM)
PMONX969_10820
PMOTX970_10475
SNANI6N98_04605
BXEBxe_A3561
BXBDR64_1260
APETToN1_06990
Reference
1  [PMID:9150211]
  Authors
Eaton RW.
  Title
p-Cymene catabolic pathway in Pseudomonas putida F1: cloning and characterization of DNA encoding conversion of p-cymene to p-cumate.
  Journal
J Bacteriol 179:3171-80 (1997)
DOI:10.1128/JB.179.10.3171-3180.1997
  Sequence
Reference
2  [PMID:9144566]
  Authors
Dutta TK, Gunsalus IC
  Title
Reductase gene sequences and protein structures: p-cymene methyl hydroxylase.
  Journal
Biochem Biophys Res Commun 233:502-6 (1997)
DOI:10.1006/bbrc.1997.6493
Reference
3  [PMID:11341314]
  Authors
Nishio T, Patel A, Wang Y, Lau PC
  Title
Biotransformations catalyzed by cloned p-cymene monooxygenase from Pseudomonas putida F1.
  Journal
Appl Microbiol Biotechnol 55:321-5 (2001)
DOI:10.1007/s002530000584
Reference
4  [PMID:21035544]
  Authors
Dutta TK, Chakraborty J, Roy M, Ghosal D, Khara P, Gunsalus IC
  Title
Cloning and characterization of a p-cymene monooxygenase from Pseudomonas chlororaphis subsp. aureofaciens.
  Journal
Res Microbiol 161:876-82 (2010)
DOI:10.1016/j.resmic.2010.10.008
Other DBs
ExplorEnz - The Enzyme Database: 1.14.15.25
IUBMB Enzyme Nomenclature: 1.14.15.25
ExPASy - ENZYME nomenclature database: 1.14.15.25
BRENDA, the Enzyme Database: 1.14.15.25

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