Information on EC 1.14.13.82 - vanillate monooxygenase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.14.13.82
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RECOMMENDED NAME
GeneOntology No.
vanillate monooxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
vanillate + O2 + NADH + H+ = 3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
show the reaction diagram
Forms part of the vanillin degradation pathway in Arthrobacter sp.
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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redox reaction
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reduction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
vanillin and vanillate degradation II
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Aminobenzoate degradation
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Microbial metabolism in diverse environments
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SYSTEMATIC NAME
IUBMB Comments
vanillate:oxygen oxidoreductase (demethylating)
Forms part of the vanillin degradation pathway in Arthrobacter sp.
CAS REGISTRY NUMBER
COMMENTARY hide
39307-11-4
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
strain HR199
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
strain SYK-6, gene ligM
SwissProt
Manually annotated by BRENDA team
strain SYK-6, gene ligM
SwissProt
Manually annotated by BRENDA team
strain NL15-2K, genes vanA and vanB
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Manually annotated by BRENDA team
strain NL15-2K, genes vanA and vanB
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Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
3,4,5-trimethoxybenzoate + O2 + NADH
3-hydroxy-4,5-dimethoxybenzoate + NAD+ + H2O + formaldehyde
show the reaction diagram
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70% of the activity compared to vanillate
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?
3,4-dimethoxybenzoate + O2 + NADH
isovanillate + NAD+ + H2O + formaldehyde
show the reaction diagram
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?
3-(hydroxymethyl)-benzoate + NAD+ + H2O + formaldehyde
m-toluate + O2 + NADH
show the reaction diagram
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?
3-hydroxymethyl-4-hydroxy-5-methylbenzoate + NADH + H2O + formaldehyde
4-hydroxy-3,5-dimethylbenzoate + O2 + NADH
show the reaction diagram
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85% of the activity compared to vanillate
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?
3-O-methylgallate + NADH + O2
?
show the reaction diagram
dicamba + O2 + electron donor + tetrahydrofolate
? + oxidized electron donor + H2O + methyltetrahydrofolate
show the reaction diagram
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titanium III citrate can act as electron donor, inducible three-component system consisting of MtvA, MtvB and MtvC, that catalyzes methyl transfer from vanillate to tetrahydrofolate
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?
isovanillic acid + NAD(P)H + O2
protocatechuic acid + NAD(P)+ + H2O + formaldehyde
show the reaction diagram
m-anisate + O2 + NADH
m-hydroxybenzoate + NAD+ + H2O + formaldehyde
show the reaction diagram
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?
vanillate + O2 + electron donor + tetrahydrofolate
3,4-dihydroxybenzoate + oxidized electron donor + H2O + methyltetrahydrofolate
show the reaction diagram
vanillate + O2 + NAD(P)H + H+
3,4-dihydroxybenzoate + NAD(P)+ + H2O + formaldehyde
show the reaction diagram
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?
vanillate + O2 + NADH
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
show the reaction diagram
vanillate + O2 + NADH + H+
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
show the reaction diagram
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?
vanillic acid + NAD(P)H + O2
protocatechuic acid + NAD(P)+ + H2O + formaldehyde
show the reaction diagram
vanillic acid + NADH + O2
protocatechuic acid + NAD+ + H2O + formaldehyde
show the reaction diagram
veratric acid + NAD(P)H + O2
isovanillic acid + NAD(P)+ + H2O + formaldehyde
show the reaction diagram
veratric acid + NAD(P)H + O2
vanillic acid + NAD(P)+ + H2O + formaldehyde
show the reaction diagram
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
isovanillic acid + NAD(P)H + O2
protocatechuic acid + NAD(P)+ + H2O + formaldehyde
show the reaction diagram
vanillate + O2 + electron donor + tetrahydrofolate
3,4-dihydroxybenzoate + oxidized electron donor + H2O + methyltetrahydrofolate
show the reaction diagram
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?
vanillate + O2 + NAD(P)H + H+
3,4-dihydroxybenzoate + NAD(P)+ + H2O + formaldehyde
show the reaction diagram
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?
vanillate + O2 + NADH
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
show the reaction diagram
vanillate + O2 + NADH + H+
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
show the reaction diagram
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?
vanillic acid + NAD(P)H + O2
protocatechuic acid + NAD(P)+ + H2O + formaldehyde
show the reaction diagram
vanillic acid + NADH + O2
protocatechuic acid + NAD+ + H2O + formaldehyde
show the reaction diagram
veratric acid + NAD(P)H + O2
isovanillic acid + NAD(P)+ + H2O + formaldehyde
show the reaction diagram
veratric acid + NAD(P)H + O2
vanillic acid + NAD(P)+ + H2O + formaldehyde
show the reaction diagram
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NAD(P)H
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Fe2+
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binding sequence motif of iron-sulfur cluster, overview
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
4-hydroxy-3,5-dimethylbenzoate
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20% competitive inhibition at 3 mM
m-anisate
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15-77.5% competitive inhibition of vanillate demethylation between 1-3 mM
m-toluate
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45% competitive inhibition at 3 mM
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
tetrahydrofolate
dependent on
additional information
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
9
dicamba
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55C, pH 6.6
0.085
vanillate
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55C, pH 6.6
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.003 - 0.88
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recombinant whole cell activities with both cofactors NADPH or NADH
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
additional information
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
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x * 43000, VanA oxygenase subunit, SDS-PAGE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli
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expressed in Escherichia coli BL21(DE3) cells
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expression in Escherichia coli
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gene ivaA, DNA and amino acid sequence determination and analysis, genetic organization, physical map, expression analysis, recombinant expression in Escherichia coli; gene ivaB, DNA and amino acid sequence determination and analysis, genetic organization, physical map, expression analysis, recombinant expression in Escherichia coli; gene vanA, DNA and amino acid sequence determination and analysis, genetic organization, physical map, expression analysis, recombinant expression in Escherichia coli
gene ligM, DNA and amino acid sequence determination and analysis, functional expression in Escherichia coli strains JM109 and BL21(DE3)
genes vanA and vanB, DNA and amino acid sequence determination and analysis, functional coexpression of genes vanA and vanB in Escherichia coli K12 strain WV1181
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genes vanA and vanB, DNA and amino acid sequence determination and analysis, genetic organization, sequence comparison, functional coexpression of genes vanA and vanB in Streptomyces lividans strain 1326 from the high-copy plasmid pIJ702, selection on veratric acid
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
during growth on vanillin or vanillate, the gene vanA is 210fold and 1200fold upregulated, respectively
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
H156R
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substituting an iron-binding ligand
W217R
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functional at 22C but not at 37C
additional information
Show AA Sequence (415 entries)
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