KEGG   ORTHOLOGY: K15757
Entry
K15757                      KO                                     
Symbol
xylM
Name
toluene methyl-monooxygenase [EC:1.14.15.26]
Pathway
map00622  Xylene degradation
map00623  Toluene degradation
map01100  Metabolic pathways
map01120  Microbial metabolism in diverse environments
map01220  Degradation of aromatic compounds
Module
M00537  Xylene degradation, xylene => methylbenzoate
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09111 Xenobiotics biodegradation and metabolism
   00623 Toluene degradation
    K15757  xylM; toluene methyl-monooxygenase
   00622 Xylene degradation
    K15757  xylM; toluene methyl-monooxygenase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.15  With reduced iron-sulfur protein as one donor, and incorporation of one atom of oxygen into the other donor
    1.14.15.26  toluene methyl-monooxygenase
     K15757  xylM; toluene methyl-monooxygenase
Other DBs
RN: R02550 R05288 R05442 R05443
GO: 0018639
Genes
PSD: DSC_14810
NAR: Saro_3845
NPP: PP1Y_AT31329
SBAR: H5V43_22380
SPHY: CHN51_07015
AG: AAA26026(xylM)
Reference
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
  Sequence
LinkDB

KEGG   ORTHOLOGY: K15758
Entry
K15758                      KO                                     
Symbol
xylA
Name
toluene methyl-monooxygenase electron transfer component [EC:1.18.1.3]
Pathway
map00622  Xylene degradation
map00623  Toluene degradation
map01100  Metabolic pathways
map01120  Microbial metabolism in diverse environments
map01220  Degradation of aromatic compounds
Module
M00537  Xylene degradation, xylene => methylbenzoate
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09111 Xenobiotics biodegradation and metabolism
   00623 Toluene degradation
    K15758  xylA; toluene methyl-monooxygenase electron transfer component
   00622 Xylene degradation
    K15758  xylA; toluene methyl-monooxygenase electron transfer component
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.18  Acting on iron-sulfur proteins as donors
   1.18.1  With NAD+ or NADP+ as acceptor
    1.18.1.3  ferredoxin---NAD+ reductase
     K15758  xylA; toluene methyl-monooxygenase electron transfer component
Other DBs
RN: R02550 R05288 R05442 R05443
GO: 0018639
Genes
PSD: DSC_14805
NAR: Saro_3846
NPP: PP1Y_AT15752 PP1Y_AT31343
SPHY: CHN51_07010
AG: AAA26027(xylA)
Reference
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
  Sequence
LinkDB

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
PSDDSC_14810
NARSaro_3845
NPPPP1Y_AT31329
SBARH5V43_22380
SPHYCHN51_07015
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
LinkDB

KEGG   REACTION: R05288
Entry
R05288                      Reaction                               
Name
p-xylene, ferredoxin:oxygen oxidoreductase (methyl-hydroxylating)
Definition
p-Xylene + Oxygen + 2 Reduced ferredoxin + 2 H+ <=> 4-Methylbenzyl alcohol + 2 Oxidized ferredoxin + H2O
Equation
Reaction class
RC00269  C06756_C06757
Enzyme
Pathway
rn00622  Xylene degradation
rn01100  Metabolic pathways
rn01120  Microbial metabolism in diverse environments
rn01220  Degradation of aromatic compounds
Module
M00537  Xylene degradation, xylene => methylbenzoate
Orthology
K15757  toluene methyl-monooxygenase [EC:1.14.15.26]
K15758  toluene methyl-monooxygenase electron transfer component [EC:1.18.1.3]
Other DBs
RHEA: 51599
LinkDB

DBGET integrated database retrieval system