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
vanillate O-demethylase oxygenase subunits A and B
Q8FRX4 AND Q8FRX3
UniProt
Manually annotated by BRENDA team
vanillate O-demethylase oxygenase subunits A and B
Q8FRX4 AND Q8FRX3
UniProt
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
genes vanA and vanB
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Manually annotated by BRENDA team
vanillate O-demethylase oxygenase subunits A and B
Q08KC3 AND Q08KC3
UniProt
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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?
4-hydroxy-3-methylbenzoate + O2 + NADH + H+
4-hydroxy-3-(hydroxymethyl)benzoate + NAD+ + H2O + formaldehyde
show the reaction diagram
Q08KC3 AND Q08KC3
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?
4-hydroxy-3-methylbenzoate + O2 + NADH + H+
?
show the reaction diagram
Q08KC3 AND Q08KC3
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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
syringate + NADH + O2
3,4-dihydroxy-5-methoxybenzoate + gallate + NAD+ + H2O + formaldehyde
show the reaction diagram
Q08KC3 AND Q08KC3
3,4-dihydroxy-5-methoxybenzoate, and gallate are produced from syringate, one of the two methoxy groups in the meta-position of syringate is demethylated first, and then the second methoxy group is demethylated at a slower rate
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?
syringate + NADH + O2
?
show the reaction diagram
Q08KC3 AND Q08KC3
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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
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
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procatechuic acid is 3,4-dihydroxybenzoate
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?
veratrate + NADH + O2
isovanillate + 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
4-hydroxy-3-methylbenzoate + O2 + NADH + H+
?
show the reaction diagram
Q08KC3 AND Q08KC3
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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
Q08KC3 AND Q08KC3
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?
syringate + NADH + O2
?
show the reaction diagram
Q08KC3 AND Q08KC3
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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
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
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procatechuic acid is 3,4-dihydroxybenzoate
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?
veratrate + NADH + O2
isovanillate + NAD+ + H2O + formaldehyde
show the reaction diagram
Q08KC3 AND Q08KC3
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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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the enzyme forms a vanillate demethylase complex of VanA, a terminal oxygenase subunit, with VanB, a ferredoxin-like subunit, performing demethylation of vanillic acid and veratric acid
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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
additional information
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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
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
additional information
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
43000
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x * 43000, VanA oxygenase subunit, SDS-PAGE
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 vanAB, recombinant overexpression in Corynebacterium glutamicum strain F, and the strain produces vanillate from ferulic acid and the enzyme converts it to protocatechiuc acid, a precursor of polymers and plastics and a constituent of food, fed-batch biotransformation
Q8FRX4 AND Q8FRX3
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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genes vanAB, functional expression in Escherichia coli strain BL21(DE3), subcloning in Escherichia coli strain DH5alpha, VanA is expressed as a soluble protein, whereas VanB is expressed in inclusion bodies
Q08KC3 AND Q08KC3
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 (402 entries)
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