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MetaCyc Enzyme: toluene ortho-monooxygenase

Synonyms: toluene 2-monooxygenase

Species: Burkholderia cepacia

Subunit composition of toluene ortho-monooxygenase = [(TomA3)2(TomA1)2(TomA4)2][TomA5][TomA2]
         toluene ortho-monooxygenase hydroxylase = (TomA3)2(TomA1)2(TomA4)2 (summary available)
                 toluene ortho-monooxygenase hydroxylase TomA3 subunit = TomA3
                 toluene ortho-monooxygenase hydroxylase TomA1 subunit = TomA1
                 toluene ortho-monooxygenase hydroxylase TomA4 subunit = TomA4
         toluene ortho-monooxygenase TomA5 subunit = TomA5 (summary available)
         toluene ortho-monooxygenase TomA2 subunit = TomA2 (summary available)

Summary:
This 3-component enzyme system belongs to a class of nonheme, oxygen-dependent diiron enzymes. It has been used in protein engineering for bioremediation of environmental pollutants [Canada02]. The 211 kD hydroxylase component contains two catalytic oxygen bridged binuclear iron centers. The 40 kD component is a NADH-oxidoreductase containing a [2Fe2S] cluster. The 10.4 kD component is a protein with no enzyme function, but is involved in electron transfer between the hydroxylase and reductase components. In contrast, other bacterial multicomponent oxygenases that oxidize aromatic compounds have an iron-sulfur cluster in the hydroxylase component, a flavin-containing reductase, and a small ferredoxin component [Newman95].

Gene-Reaction Schematic: ?


Enzymatic reaction of: cresol ortho-monooxygenase (toluene ortho-monooxygenase)

EC Number: 1.14.13.-

2-methylphenol + NADH + H+ + oxygen <=> 3-methylcatechol + NAD+ + H2O

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the direction in which it was curated.

The reaction is physiologically favored in the direction shown.

In Pathways: superpathway of aerobic toluene degradation , toluene degradation I (aerobic) (via o-cresol) , toluene degradation to 2-oxopent-4-enoate I (via o-cresol)

Summary:
Toluene ortho-monooxygenase dihydroxylates toluene in two sequential hydroxylations. The first hydroxylation is in the ortho-position, yielding o-cresol, and the second is in the meta-position, yielding 2,3-dihydroxytoluene. The reductase component requires FAD as a cofactor [Newman95]. The enzyme was inactivated in vivo by alkynes [Yeager99].

Cofactors or Prosthetic Groups: FAD [Newman95]


Enzymatic reaction of: toluene ortho-monooxygenase

EC Number: 1.14.13.-

toluene + NADH + H+ + oxygen <=> 2-methylphenol + NAD+ + H2O

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the direction in which it was curated.

The reaction is physiologically favored in the direction shown.

In Pathways: superpathway of aerobic toluene degradation , toluene degradation I (aerobic) (via o-cresol) , toluene degradation to 2-oxopent-4-enoate I (via o-cresol)

Summary:
Toluene ortho-monooxygenase dihydroxylates toluene in two sequential hydroxylations. The first hydroxylation is in the ortho-position, yielding o-cresol, and the second is in the meta-position, yielding 2,3-dihydroxytoluene. The reductase component requires FAD as a cofactor [Newman95]. The enzyme was inactivated in vivo by alkynes [Yeager99].

Cofactors or Prosthetic Groups: FAD [Newman95]


Subunit of toluene ortho-monooxygenase: toluene ortho-monooxygenase hydroxylase

Molecular Weight: 211 kD (experimental) [Newman95]

Summary:
Toluene ortho-monooxygenase hydroxylase is part of the 3-component toluene ortho-monooxygenase (toluene 2-monooxygenase) enzyme system [Newman95].


Subunit of toluene ortho-monooxygenase hydroxylase: toluene ortho-monooxygenase hydroxylase TomA3 subunit

Gene: tomA3 Accession Number: G-8601 (MetaCyc)

Molecular Weight: 54.5 kD (experimental) [Newman95]

Unification Links: ModBase:Q8VSV8 , Protein Model Portal:Q8VSV8 , SMR:Q8VSV8 , Swiss-Model:Q8VSV8 , UniProt:Q8VSV8

Relationship Links: InterPro:IN-FAMILY:IPR003430 , InterPro:IN-FAMILY:IPR007029 , InterPro:IN-FAMILY:IPR009078 , InterPro:IN-FAMILY:IPR012348 , Pfam:IN-FAMILY:PF02332 , Pfam:IN-FAMILY:PF04945


Subunit of toluene ortho-monooxygenase hydroxylase: toluene ortho-monooxygenase hydroxylase TomA1 subunit

Gene: tomA1 Accession Number: G-8602 (MetaCyc)

Molecular Weight: 37.7 kD (experimental) [Newman95]

Unification Links: ModBase:Q9ANX4 , Protein Model Portal:Q9ANX4 , Swiss-Model:Q9ANX4 , UniProt:Q9ANX4

Relationship Links: InterPro:IN-FAMILY:IPR003430 , InterPro:IN-FAMILY:IPR009078 , InterPro:IN-FAMILY:IPR012078 , InterPro:IN-FAMILY:IPR012348 , Pfam:IN-FAMILY:PF02332


Subunit of toluene ortho-monooxygenase hydroxylase: toluene ortho-monooxygenase hydroxylase TomA4 subunit

Gene: tomA4 Accession Number: G-8603 (MetaCyc)

Molecular Weight: 13.5 kD (experimental) [Newman95]

Unification Links: ModBase:Q9ANX1 , Protein Model Portal:Q9ANX1 , Swiss-Model:Q9ANX1 , UniProt:Q9ANX1

Relationship Links: InterPro:IN-FAMILY:IPR006756 , Pfam:IN-FAMILY:PF04663


Subunit of toluene ortho-monooxygenase: toluene ortho-monooxygenase TomA5 subunit

Gene: tomA5 Accession Number: G-8606 (MetaCyc)

Molecular Weight: 40 kD (experimental) [Newman95]

Unification Links: ModBase:Q9ANX0 , Protein Model Portal:Q9ANX0 , Swiss-Model:Q9ANX0 , UniProt:Q9ANX0

Relationship Links: InterPro:IN-FAMILY:IPR001041 , InterPro:IN-FAMILY:IPR001221 , InterPro:IN-FAMILY:IPR001433 , InterPro:IN-FAMILY:IPR006058 , InterPro:IN-FAMILY:IPR008333 , InterPro:IN-FAMILY:IPR012675 , InterPro:IN-FAMILY:IPR017927 , InterPro:IN-FAMILY:IPR017938 , Pfam:IN-FAMILY:PF00111 , Pfam:IN-FAMILY:PF00175 , Pfam:IN-FAMILY:PF00970 , Prints:IN-FAMILY:PR00410 , Prosite:IN-FAMILY:PS00197 , Prosite:IN-FAMILY:PS51085 , Prosite:IN-FAMILY:PS51384

Summary:
The toluene ortho-monooxygenase TomA5 subunit is a component of the 3-component toluene ortho-monooxygenase (toluene 2-monooxygenase) enzyme system [Newman95].


Subunit of toluene ortho-monooxygenase: toluene ortho-monooxygenase TomA2 subunit

Gene: tomA2 Accession Number: G-8607 (MetaCyc)

Molecular Weight: 10.4 kD (experimental) [Newman95]

Unification Links: ModBase:Q9ANX3 , Protein Model Portal:Q9ANX3 , Swiss-Model:Q9ANX3 , UniProt:Q9ANX3

Relationship Links: InterPro:IN-FAMILY:IPR003454 , Pfam:IN-FAMILY:PF02406 , ProDom:IN-FAMILY:PD004249

Summary:
The toluene ortho-monooxygenase TomA2 subunit is a component of the 3-component toluene ortho-monooxygenase (toluene 2-monooxygenase) enzyme system [Newman95].


References

Canada02: Canada KA, Iwashita S, Shim H, Wood TK (2002). "Directed evolution of toluene ortho-monooxygenase for enhanced 1-naphthol synthesis and chlorinated ethene degradation." J Bacteriol 184(2);344-9. PMID: 11751810

Newman95: Newman LM, Wackett LP (1995). "Purification and characterization of toluene 2-monooxygenase from Burkholderia cepacia G4." Biochemistry 34(43);14066-76. PMID: 7578004

Shields91: Shields MS, Montgomery SO, Cuskey SM, Chapman PJ, Pritchard PH (1991). "Mutants of Pseudomonas cepacia G4 defective in catabolism of aromatic compounds and trichloroethylene." Appl Environ Microbiol 57(7);1935-41. PMID: 1892384

Shields95: Shields MS, Reagin MJ, Gerger RR, Campbell R, Somerville C (1995). "TOM, a new aromatic degradative plasmid from Burkholderia (Pseudomonas) cepacia G4." Appl Environ Microbiol 1995;61(4);1352-6. PMID: 7538275

Yeager99: Yeager CM, Bottomley PJ, Arp DJ, Hyman MR (1999). "Inactivation of toluene 2-monooxygenase in Burkholderia cepacia G4 by alkynes." Appl Environ Microbiol 65(2);632-9. PMID: 9925593


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Fri Nov 28, 2014, biocyc13.