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Enzyme Nomenclature
Information on EC 1.14.13.82 - vanillate monooxygenase
for references in articles please use BRENDA:EC1.14.13.82
Word Map on EC 1.14.13.82
- 1.14.13.82
- protocatechuate
- vanillin
-
ferulic
-
lignin
- 3,4-dihydroxybenzoate
-
o-demethylation
- corrinoid
-
acetobacterium
- dehalogenans
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The enzyme appears in viruses and cellular organisms
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EC NUMBER 
COMMENTARY 
1.14.13.82
-
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RECOMMENDED NAME
GeneOntology No.
vanillate monooxygenase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
vanillate + O2 + NADH + H+ = 3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
Forms part of the vanillin degradation pathway in Arthrobacter sp.
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-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
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SYSTEMATIC NAME
IUBMB Comments
vanillate:oxygen oxidoreductase (demethylating)
Forms part of the vanillin degradation pathway in Arthrobacter sp.
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CAS REGISTRY NUMBER
COMMENTARY
39307-11-4
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
vanillate O-demethylase oxygenase subunits A and B
Q8FRX4, Q8FRX3
UniProt
vanillate O-demethylase oxygenase subunits A and B
Q8FRX4, Q8FRX3
UniProt
vanillate O-demethylase oxygenase subunits A and B
Q08KC3, Q08KC3
UniProt
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
3,4,5-trimethoxybenzoate + O2 + NADH
3-hydroxy-4,5-dimethoxybenzoate + NAD+ + H2O + formaldehyde
-
70% of the activity compared to vanillate
-
?
3,4-dimethoxybenzoate + O2 + NADH
isovanillate + NAD+ + H2O + formaldehyde
-
-
-
?
3-(hydroxymethyl)-benzoate + NAD+ + H2O + formaldehyde
m-toluate + O2 + NADH
-
-
-
?
3-hydroxymethyl-4-hydroxy-5-methylbenzoate + NADH + H2O + formaldehyde
4-hydroxy-3,5-dimethylbenzoate + O2 + NADH
-
85% of the activity compared to vanillate
-
?
4-hydroxy-3-methylbenzoate + O2 + NADH + H+
4-hydroxy-3-(hydroxymethyl)benzoate + NAD+ + H2O + formaldehyde
Q08KC3; Q08KC3;
-
-
-
?
4-hydroxy-3-methylbenzoate + O2 + NADH + H+
?
Q08KC3; Q08KC3;
-
-
-
?
syringate + NADH + O2
3,4-dihydroxy-5-methoxybenzoate + gallate + NAD+ + H2O + formaldehyde
Q08KC3; 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
-
-
?
vanillate + O2 + NAD(P)H + H+
3,4-dihydroxybenzoate + NAD(P)+ + H2O + formaldehyde
-
-
-
-
?
vanillic acid + NADH + O2
protocatechuic acid + NAD+ + H2O + formaldehyde
-
-
procatechuic acid is 3,4-dihydroxybenzoate
-
?
isovanillic acid + NAD(P)H + O2
protocatechuic acid + NAD(P)+ + H2O + formaldehyde
O-demethylation by IvaAB
-
-
?
isovanillic acid + NAD(P)H + O2
protocatechuic acid + NAD(P)+ + H2O + formaldehyde
i.e. 3-hydroxy-4-methoxybenzoate, O-demethylation by IvaAB
procatechuic acid is 3,4-dihydroxybenzoate
-
?
isovanillic acid + NAD(P)H + O2
protocatechuic acid + NAD(P)+ + H2O + formaldehyde
O-demethylation by IvaAB
-
-
?
isovanillic acid + NAD(P)H + O2
protocatechuic acid + NAD(P)+ + H2O + formaldehyde
i.e. 3-hydroxy-4-methoxybenzoate, O-demethylation by IvaAB
procatechuic acid is 3,4-dihydroxybenzoate
-
?
m-anisate + O2 + NADH
m-hydroxybenzoate + NAD+ + H2O + formaldehyde
-
-
-
?
m-anisate + O2 + NADH
m-hydroxybenzoate + NAD+ + H2O + formaldehyde
Q08KC3; Q08KC3;
-
-
-
?
vanillate + O2 + NADH
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
-
-
-
-
vanillate + O2 + NADH
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
-
able to demethylate one methoxy group or to monohydroxylate one methyl group in the meta position
-
r
vanillate + O2 + NADH
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
-
-
-
-
?
vanillate + O2 + NADH
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
-
-
-
?
vanillate + O2 + NADH
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
-
-
-
?
vanillate + O2 + NADH + H+
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
Q8FRX4; Q8FRX3;
i.e. protocatechiuc acid
-
-
?
vanillate + O2 + NADH + H+
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
Q8FRX4; Q8FRX3;
i.e. protocatechiuc acid
-
-
?
vanillate + O2 + NADH + H+
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
-
-
-
-
?
vanillate + O2 + NADH + H+
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
Q08KC3; Q08KC3;
i.e. protocatechiuc acid
-
-
?
vanillic acid + NAD(P)H + O2
protocatechuic acid + NAD(P)+ + H2O + formaldehyde
O-demethylation by VanA
-
-
?
vanillic acid + NAD(P)H + O2
protocatechuic acid + NAD(P)+ + H2O + formaldehyde
i.e. 4-hydroxy-3-methoxybenzoate, O-demethylation by VanA
procatechuic acid is 3,4-dihydroxybenzoate
-
?
vanillic acid + NAD(P)H + O2
protocatechuic acid + NAD(P)+ + H2O + formaldehyde
O-demethylation by VanA
-
-
?
vanillic acid + NAD(P)H + O2
protocatechuic acid + NAD(P)+ + H2O + formaldehyde
i.e. 4-hydroxy-3-methoxybenzoate, O-demethylation by VanA
procatechuic acid is 3,4-dihydroxybenzoate
-
?
vanillic acid + NAD(P)H + O2
protocatechuic acid + NAD(P)+ + H2O + formaldehyde
-
-
procatechuic acid is 3,4-dihydroxybenzoate
-
?
vanillic acid + NAD(P)H + O2
protocatechuic acid + NAD(P)+ + H2O + formaldehyde
-
functional coupling between vanillate-O-demethylase and formaldehyde detoxification pathway, formaldehyde is further converted to formate by glutathione-dependent formaldehyde dehydrogenase, encoded by gene frmA
procatechuic acid is 3,4-dihydroxybenzoate
-
?
veratrate + NADH + O2
isovanillate + NAD+ + H2O + formaldehyde
Q08KC3; Q08KC3;
-
-
-
-
veratrate + NADH + O2
isovanillate + NAD+ + H2O + formaldehyde
Q08KC3; Q08KC3;
demethylation product of veratrate is isovanillate rather than vanillate, 1H-NMR analysis. O-Demethylation of veratrate by Streptomyces vanillate demethylase occurs only at the meta-position relative to the carboxyl group
-
-
?
veratric acid + NAD(P)H + O2
isovanillic acid + NAD(P)+ + H2O + formaldehyde
O-demethylation by VanA
-
-
?
veratric acid + NAD(P)H + O2
isovanillic acid + NAD(P)+ + H2O + formaldehyde
i.e. 3,4-dimethoxybenzoate, O-demethylation by VanA
-
-
?
veratric acid + NAD(P)H + O2
isovanillic acid + NAD(P)+ + H2O + formaldehyde
O-demethylation by VanA
-
-
?
veratric acid + NAD(P)H + O2
isovanillic acid + NAD(P)+ + H2O + formaldehyde
i.e. 3,4-dimethoxybenzoate, O-demethylation by VanA
-
-
?
veratric acid + NAD(P)H + O2
vanillic acid + NAD(P)+ + H2O + formaldehyde
O-demethylation by IvaAB
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-
?
veratric acid + NAD(P)H + O2
vanillic acid + NAD(P)+ + H2O + formaldehyde
i.e. 3,4-dimethoxybenzoate, O-demethylation by IvaAB
-
-
?
veratric acid + NAD(P)H + O2
vanillic acid + NAD(P)+ + H2O + formaldehyde
O-demethylation by IvaAB
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-
?
veratric acid + NAD(P)H + O2
vanillic acid + NAD(P)+ + H2O + formaldehyde
i.e. 3,4-dimethoxybenzoate, O-demethylation by IvaAB
-
-
?
additional information
?
-
-
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
-
-
-
additional information
?
-
Q08KC3; Q08KC3;
substrate specificity for vanillate analogues by an in vivo assay using recombinant whole cells: among aromatic methyl ethers, vanillate, syringate, m-anisate, and veratrate are good substrates, whereas ferulate, vanillin, and guaiacol are not recognized by Streptomyces vanillate demethylase. Besides vanillate, 4-hydroxy-3-methylbenzoate is a better substrate than m-anisate and veratrate, and the 3-methyl group is efficiently oxidized to a hydroxymethyl group. The combination of a carboxyl group on the benzene ring and a hydroxyl group in the para-position relative to the carboxyl group may be preferable for substrate recognition by the enzyme. Demethylation by Streptomyces vanillate demethylase occurs only at the 3-position of veratrate and not at the 4-position
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-
-
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
4-hydroxy-3-methylbenzoate + O2 + NADH + H+
?
Q08KC3 AND Q08KC3
-
-
-
?
m-anisate + O2 + NADH
m-hydroxybenzoate + NAD+ + H2O + formaldehyde
Q08KC3 AND Q08KC3
-
-
-
?
vanillate + O2 + NAD(P)H + H+
3,4-dihydroxybenzoate + NAD(P)+ + H2O + formaldehyde
-
-
-
-
?
vanillic acid + NADH + O2
protocatechuic acid + NAD+ + H2O + formaldehyde
-
-
procatechuic acid is 3,4-dihydroxybenzoate
-
?
veratrate + NADH + O2
isovanillate + NAD+ + H2O + formaldehyde
Q08KC3 AND Q08KC3
-
-
-
-
additional information
?
-
-
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
-
-
-
isovanillic acid + NAD(P)H + O2
protocatechuic acid + NAD(P)+ + H2O + formaldehyde
Q2KQ78, Q2KQ79, Q2KQ82
O-demethylation by IvaAB
-
-
?
isovanillic acid + NAD(P)H + O2
protocatechuic acid + NAD(P)+ + H2O + formaldehyde
Q2KQ78, Q2KQ79, Q2KQ82
O-demethylation by IvaAB
-
-
?
vanillate + O2 + NADH
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
-
-
-
-
vanillate + O2 + NADH
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
-
able to demethylate one methoxy group or to monohydroxylate one methyl group in the meta position
-
r
vanillate + O2 + NADH
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
-
-
-
-
?
vanillate + O2 + NADH
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
-
-
-
?
vanillate + O2 + NADH
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
-
-
-
?
vanillate + O2 + NADH + H+
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
Q8FRX4 AND Q8FRX3
i.e. protocatechiuc acid
-
-
?
vanillate + O2 + NADH + H+
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
Q8FRX4 AND Q8FRX3
i.e. protocatechiuc acid
-
-
?
vanillate + O2 + NADH + H+
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
-
-
-
-
?
vanillate + O2 + NADH + H+
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
Q08KC3 AND Q08KC3
i.e. protocatechiuc acid
-
-
?
vanillic acid + NAD(P)H + O2
protocatechuic acid + NAD(P)+ + H2O + formaldehyde
Q2KQ78, Q2KQ79, Q2KQ82
O-demethylation by VanA
-
-
?
vanillic acid + NAD(P)H + O2
protocatechuic acid + NAD(P)+ + H2O + formaldehyde
Q2KQ78, Q2KQ79, Q2KQ82
O-demethylation by VanA
-
-
?
vanillic acid + NAD(P)H + O2
protocatechuic acid + NAD(P)+ + H2O + formaldehyde
-
functional coupling between vanillate-O-demethylase and formaldehyde detoxification pathway, formaldehyde is further converted to formate by glutathione-dependent formaldehyde dehydrogenase, encoded by gene frmA
procatechuic acid is 3,4-dihydroxybenzoate
-
?
veratric acid + NAD(P)H + O2
isovanillic acid + NAD(P)+ + H2O + formaldehyde
Q2KQ78, Q2KQ79, Q2KQ82
O-demethylation by VanA
-
-
?
veratric acid + NAD(P)H + O2
isovanillic acid + NAD(P)+ + H2O + formaldehyde
Q2KQ78, Q2KQ79, Q2KQ82
O-demethylation by VanA
-
-
?
veratric acid + NAD(P)H + O2
vanillic acid + NAD(P)+ + H2O + formaldehyde
Q2KQ78, Q2KQ79, Q2KQ82
O-demethylation by IvaAB
-
-
?
veratric acid + NAD(P)H + O2
vanillic acid + NAD(P)+ + H2O + formaldehyde
Q2KQ78, Q2KQ79, Q2KQ82
O-demethylation by IvaAB
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
m-anisate
-
15-77.5% competitive inhibition of vanillate demethylation between 1-3 mM
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
the enzyme is inducible by vanillic acid and veratric acid; the enzyme is inducible by vanillic acid and veratric acid; the enzyme is inducible by vanillic acid and veratric acid
-
additional information
the enzyme is inducible by vanillic acid and veratric acid; the enzyme is inducible by vanillic acid and veratric acid; the enzyme is inducible by vanillic acid and veratric acid
-
additional information
the enzyme is inducible by vanillic acid and veratric acid; the enzyme is inducible by vanillic acid and veratric acid; the enzyme is inducible by vanillic acid and veratric acid
-
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.003 - 0.88
-
recombinant whole cell activities with both cofactors NADPH or NADH
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
additional information
additional information
in succinate- and procatechuic acid-grown cells, there is negligible degradative activity towards vanillic acid, veratric acid, and isovanillic acid and little to no expression of genes vanA, ivaA, and ivaB, growth on vanillic acid or veratric acid results in production of active oxygenases and expression of vanA, ivaA, and ivaB; in succinate- and procatechuic acid-grown cells, there is negligible degradative activity towards vanillic acid, veratric acid, and isovanillic acid and little to no expression of genes vanA, ivaA, and ivaB, growth on vanillic acid or veratric acid results in production of active oxygenases and expression of vanA, ivaA, and ivaB; in succinate- and procatechuic acid-grown cells, there is negligible degradative activity towards vanillic acid, veratric acid, and isovanillic acid and little to no expression of genes van, ivaA, and ivaB, growth on vanillic acid or veratric acid results in production of active oxygenases and expression of vanA, ivaA, and ivaB
additional information
in succinate- and procatechuic acid-grown cells, there is negligible degradative activity towards vanillic acid, veratric acid, and isovanillic acid and little to no expression of genes vanA, ivaA, and ivaB, growth on vanillic acid or veratric acid results in production of active oxygenases and expression of vanA, ivaA, and ivaB; in succinate- and procatechuic acid-grown cells, there is negligible degradative activity towards vanillic acid, veratric acid, and isovanillic acid and little to no expression of genes vanA, ivaA, and ivaB, growth on vanillic acid or veratric acid results in production of active oxygenases and expression of vanA, ivaA, and ivaB; in succinate- and procatechuic acid-grown cells, there is negligible degradative activity towards vanillic acid, veratric acid, and isovanillic acid and little to no expression of genes van, ivaA, and ivaB, growth on vanillic acid or veratric acid results in production of active oxygenases and expression of vanA, ivaA, and ivaB
additional information
in succinate- and procatechuic acid-grown cells, there is negligible degradative activity towards vanillic acid, veratric acid, and isovanillic acid and little to no expression of genes vanA, ivaA, and ivaB, growth on vanillic acid or veratric acid results in production of active oxygenases and expression of vanA, ivaA, and ivaB; in succinate- and procatechuic acid-grown cells, there is negligible degradative activity towards vanillic acid, veratric acid, and isovanillic acid and little to no expression of genes vanA, ivaA, and ivaB, growth on vanillic acid or veratric acid results in production of active oxygenases and expression of vanA, ivaA, and ivaB; in succinate- and procatechuic acid-grown cells, there is negligible degradative activity towards vanillic acid, veratric acid, and isovanillic acid and little to no expression of genes van, ivaA, and ivaB, growth on vanillic acid or veratric acid results in production of active oxygenases and expression of vanA, ivaA, and ivaB
additional information
-
in succinate- and procatechuic acid-grown cells, there is negligible degradative activity towards vanillic acid, veratric acid, and isovanillic acid and little to no expression of genes vanA, ivaA, and ivaB, growth on vanillic acid or veratric acid results in production of active oxygenases and expression of vanA, ivaA, and ivaB; in succinate- and procatechuic acid-grown cells, there is negligible degradative activity towards vanillic acid, veratric acid, and isovanillic acid and little to no expression of genes vanA, ivaA, and ivaB, growth on vanillic acid or veratric acid results in production of active oxygenases and expression of vanA, ivaA, and ivaB; in succinate- and procatechuic acid-grown cells, there is negligible degradative activity towards vanillic acid, veratric acid, and isovanillic acid and little to no expression of genes van, ivaA, and ivaB, growth on vanillic acid or veratric acid results in production of active oxygenases and expression of vanA, ivaA, and ivaB
-
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
dimer
dimer
presence of both subunits is essential; presence of both subunits is essential; presence of both subunits is essential
dimer
-
presence of both subunits is essential; presence of both subunits is essential; presence of both subunits is essential
-
dimer
Q08KC3; Q08KC3;
1 x 40000, subunit A + 1 * 33000, subunit B, recombinant enzyme, SDS-PAGE
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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; 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
-
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
-
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; Q08KC3;
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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
LITERATURE
additional information
additional information
-
several amino acid substitutions give indications of the extent to which amino acid substitutions can be tolerated at specified positions
additional information
Q8FRX4; Q8FRX3;
generation of recombinant Corynebacterium glutamicum strain F, overexpression of vanillate O-demethylase (VanAB) to increase the production of protocatechiuc acid from ferulic acid. The strain FVan 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, protocatechiuc acid is secreted to the medium, overview
additional information
-
generation of recombinant Corynebacterium glutamicum strain F, overexpression of vanillate O-demethylase (VanAB) to increase the production of protocatechiuc acid from ferulic acid. The strain FVan 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, protocatechiuc acid is secreted to the medium, overview
-
additional information
-
the reaction of the recombinant enzyme is one of the limiting steps of the prospective bioconversion from lignin-derived compounds to valuable products in recombinant Escherichia coli
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