KEGG ORTHOLOGY: K15757

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

Reaction

R02550

toluene,ferredoxin:oxygen oxidoreductase (methyl-hydroxylating)

R05288

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

R05442

o-xylene,ferredoxin:oxygen oxidoreductase (methyl-hydroxylating)

R05443

m-xylene,ferredoxin:oxygen oxidoreductase (methyl-hydroxylating)

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

GO:

0018639

Genes

PSD:

DSC_14810

NAR:

Saro_3845

NPP:	PP1Y_AT31329

SBAR:

H5V43_22380

SPHY:

CHN51_07015

MAUS:

JN090_26195

RPSK:

JWS13_01880 JWS13_02030

PPEL:

H6H00_18580

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

[ag:AAA26026]

LinkDB

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

Reaction

R02550

toluene,ferredoxin:oxygen oxidoreductase (methyl-hydroxylating)

R05288

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

R05442

o-xylene,ferredoxin:oxygen oxidoreductase (methyl-hydroxylating)

R05443

m-xylene,ferredoxin:oxygen oxidoreductase (methyl-hydroxylating)

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

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

[ag:AAA26027]

LinkDB

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

MAUS:

JN090_26195

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

LinkDB

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

C06756 + C00007 + 2 C00138 + 2 C00080 <=> C06757 + 2 C00139 + C00001

Reaction class

RC00269

C06756_C06757

Enzyme

1.14.15.26

Pathway

rn00622

Xylene degradation

rn01100

Metabolic pathways

rn01120

Microbial metabolism in diverse environments

rn01220

Degradation of aromatic compounds

Module

M00537

Xylene degradation, xylene => methylbenzoate

Brite

Enzymatic reactions [BR:br08201]
1. Oxidoreductase reactions
  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
     R05288  p-Xylene + Oxygen + 2 Reduced ferredoxin + 2 H+ <=> 4-Methylbenzyl alcohol + 2 Oxidized ferredoxin + H2O

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