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Enzyme Nomenclature
Information on EC 1.14.13.82 - vanillate monooxygenase
Word Map on EC 1.14.13.82
- 1.14.13.82
- protocatechuate
- vanillin
- ferulate
- syringate
-
bioconversion
-
lignin
-
4,5-dioxygenase
-
o-demethylation
-
acetobacterium
- corrinoid
- dehalogenans
- paucimobilis
-
rieske-type
-
sphingomonas
- 3,4-dihydroxybenzoate
-
pbluescript
-
plant-type
-
h4folate
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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
gene ivaA; strain BR6020, genes ivaA, and ivaB
SwissProt
gene ivaB; strain BR6020, genes ivaA, and ivaB
SwissProt
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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
-
?
dicamba + O2 + electron donor + tetrahydrofolate
? + oxidized electron donor + H2O + methyltetrahydrofolate
-
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
-
-
?
m-anisate + O2 + NADH
m-hydroxybenzoate + NAD+ + H2O + formaldehyde
-
-
-
?
vanillate + O2 + electron donor + tetrahydrofolate
3,4-dihydroxybenzoate + oxidized electron donor + H2O + methyltetrahydrofolate
vanillate + O2 + NAD(P)H + H+
3,4-dihydroxybenzoate + NAD(P)+ + H2O + formaldehyde
-
-
-
-
?
vanillate + O2 + NADH + H+
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
-
-
-
-
?
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
-
?
vanillate + O2 + electron donor + tetrahydrofolate
3,4-dihydroxybenzoate + oxidized electron donor + H2O + methyltetrahydrofolate
-
-
-
-
?
vanillate + O2 + electron donor + tetrahydrofolate
3,4-dihydroxybenzoate + oxidized electron donor + H2O + methyltetrahydrofolate
-
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
-
-
?
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
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
-
-
-
?
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
-
?
vanillic acid + NADH + O2
protocatechuic acid + NAD+ + H2O + formaldehyde
-
procatechuic acid is 3,4-dihydroxybenzoate, procatechuic acid is 3,4-dihydroxybenzoate, which is further degraded via the procatechiuc acid 4,5-cleavage pathway
-
?
vanillic acid + NADH + O2
protocatechuic acid + NAD+ + H2O + formaldehyde
-
procatechuic acid is 3,4-dihydroxybenzoate, procatechuic acid is 3,4-dihydroxybenzoate, which is further degraded via the procatechiuc acid 4,5-cleavage pathway
-
?
vanillic acid + NADH + O2
protocatechuic acid + NAD+ + H2O + formaldehyde
-
-
procatechuic acid is 3,4-dihydroxybenzoate, which is further degraded via the procatechiuc acid 4,5-cleavage pathway
-
?
vanillic acid + NADH + O2
protocatechuic acid + NAD+ + H2O + formaldehyde
-
-
procatechuic acid is 3,4-dihydroxybenzoate
-
?
vanillic acid + NADH + O2
protocatechuic acid + NAD+ + H2O + formaldehyde
-
-
procatechuic acid is 3,4-dihydroxybenzoate
-
?
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
-
-
?
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
-
-
?
veratric acid + NAD(P)H + O2
vanillic acid + NAD(P)+ + H2O + formaldehyde
i.e. 3,4-dimethoxybenzoate, O-demethylation by IvaAB
-
-
?
additional information
?
-
syringate is no substrate
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-
-
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
?
-
-
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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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
vanillate + O2 + electron donor + tetrahydrofolate
3,4-dihydroxybenzoate + oxidized electron donor + H2O + methyltetrahydrofolate
-
-
-
-
?
vanillate + O2 + NAD(P)H + H+
3,4-dihydroxybenzoate + NAD(P)+ + H2O + formaldehyde
-
-
-
-
?
vanillate + O2 + NADH + H+
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
-
-
-
-
?
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
3,4-dihydroxybenzoate + NAD+ + H2O + formaldehyde
-
-
-
?
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
-
?
vanillic acid + NADH + O2
protocatechuic acid + NAD+ + H2O + formaldehyde
Q60FX1
-
procatechuic acid is 3,4-dihydroxybenzoate, which is further degraded via the procatechiuc acid 4,5-cleavage pathway
-
?
vanillic acid + NADH + O2
protocatechuic acid + NAD+ + H2O + formaldehyde
Q60FX1
-
procatechuic acid is 3,4-dihydroxybenzoate, which is further degraded via the procatechiuc acid 4,5-cleavage pathway
-
?
vanillic acid + NADH + O2
protocatechuic acid + NAD+ + H2O + formaldehyde
-
-
procatechuic acid is 3,4-dihydroxybenzoate
-
?
vanillic acid + NADH + O2
protocatechuic acid + NAD+ + H2O + formaldehyde
-
-
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
-
-
?
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
?
-
-
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
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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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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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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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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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
-
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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 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
-
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
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
-
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
additional information
disruption of ligM leads to significant growth retardation on both vanillate and syringate, a ligM desA double mutant completely looses the ability to transform vanillate, phenotypes, overview
additional information
-
disruption of ligM leads to significant growth retardation on both vanillate and syringate, a ligM desA double mutant completely looses the ability to transform vanillate, phenotypes, overview
-
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LINKS TO OTHER DATABASES (specific for EC-Number 1.14.13.82)
Information
