KEGG   ENZYME: 1.14.15.26
Entry
EC 1.14.15.26               Enzyme                                 
Name
toluene methyl-monooxygenase;
xylM (gene names);
ntnM (gene names)
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
methylbenzene,ferredoxin:oxygen oxidoreductase (methyl-hydroxylating)
Reaction(IUBMB)
(1) toluene + O2 + 2 reduced ferredoxin [iron-sulfur] cluster + 2 H+ = benzyl alcohol + 2 oxidized ferredoxin [iron-sulfur] cluster + H2O [RN:R02550];
(2) p-xylene + O2 + 2 reduced ferredoxin [iron-sulfur] cluster + 2 H+ = 4-methylbenzyl alcohol + 2 oxidized ferredoxin [iron-sulfur] cluster + H2O [RN:R05288];
(3) m-xylene + O2 + 2 reduced ferredoxin [iron-sulfur] cluster + 2 H+ = 3-methylbenzyl alcohol + 2 oxidized ferredoxin [iron-sulfur] cluster + H2O [RN:R05443]
Reaction(KEGG)
R02550 R05288 R05443;
(other) R05442
Substrate
toluene [CPD:C01455];
O2 [CPD:C00007];
reduced ferredoxin [iron-sulfur] cluster [CPD:C00138];
H+ [CPD:C00080];
p-xylene [CPD:C06756];
m-xylene [CPD:C07208]
Product
benzyl alcohol [CPD:C00556];
oxidized ferredoxin [iron-sulfur] cluster [CPD:C00139];
H2O [CPD:C00001];
4-methylbenzyl alcohol [CPD:C06757];
3-methylbenzyl alcohol [CPD:C07216]
Comment
The enzyme, characterized from several Pseudomonas strains, catalyses the first step in the degradation of toluenes and xylenes. It has a broad substrate specificity and is also active with substituted compounds, such as chlorotoluenes. 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. The enzyme can also act on its products, producing gem-diols that spontaneously dehydrate to form aldehydes.
History
EC 1.14.15.26 created 2018
Pathway
ec00622  Xylene degradation
ec00623  Toluene degradation
ec01100  Metabolic pathways
ec01120  Microbial metabolism in diverse environments
Orthology
K15757  toluene methyl-monooxygenase
Genes
PSD: DSC_14810
NAR: Saro_3845
NPP: PP1Y_AT31329
SBAR: H5V43_22380
SPHY: CHN51_07015
RPSK: JWS13_01880 JWS13_02030
PPEL: H6H00_18580
Reference
1  [PMID:1999388]
  Authors
Suzuki M, Hayakawa T, Shaw JP, Rekik M, Harayama S
  Title
Primary structure of xylene monooxygenase: similarities to and differences from the alkane hydroxylation system.
  Journal
J Bacteriol 173:1690-5 (1991)
DOI:10.1128/JB.173.5.1690-1695.1991
Reference
2  [PMID:1327782]
  Authors
Shaw JP, Harayama S
  Title
Purification and characterisation of the NADH:acceptor reductase component of xylene monooxygenase encoded by the TOL plasmid pWW0 of Pseudomonas putida mt-2.
  Journal
Eur J Biochem 209:51-61 (1992)
DOI:10.1111/j.1432-1033.1992.tb17260.x
Reference
3  [PMID:1526468]
  Authors
Brinkmann U, Reineke W
  Title
Degradation of chlorotoluenes by in vivo constructed hybrid strains: problems of  enzyme specificity, induction and prevention of meta-pathway.
  Journal
FEMS Microbiol Lett 75:81-7 (1992)
DOI:10.1016/0378-1097(92)90460-6
Reference
4  [PMID:9555884]
  Authors
James KD, Williams PA
  Title
ntn genes determining the early steps in the divergent catabolism of 4-nitrotoluene and toluene in Pseudomonas sp. strain TW3.
  Journal
J Bacteriol 180:2043-9 (1998)
DOI:10.1128/JB.180.8.2043-2049.1998
Other DBs
ExplorEnz - The Enzyme Database: 1.14.15.26
IUBMB Enzyme Nomenclature: 1.14.15.26
ExPASy - ENZYME nomenclature database: 1.14.15.26
BRENDA, the Enzyme Database: 1.14.15.26

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Pathway (9)   
   KEGG PATHWAY (8)   
   KEGG MODULE (1)   
Chemical substance (13)   
   KEGG COMPOUND (13)   
Chemical reaction (5)   
   KEGG REACTION (4)   
   KEGG RCLASS (1)   
Gene (10)   
   KEGG ORTHOLOGY (1)   
   KEGG GENES (9)   
Protein sequence (2)   
   UniProt (1)   
   SWISS-PROT (1)   
Protein domain (2)   
   InterPro (2)   
All databases (41)   

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