Information on EC 1.14.13.5 - imidazoleacetate 4-monooxygenase

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The expected taxonomic range for this enzyme is: Pseudomonas sp.

EC NUMBER
COMMENTARY hide
1.14.13.5
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RECOMMENDED NAME
GeneOntology No.
imidazoleacetate 4-monooxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
4-imidazoleacetate + NADH + H+ + O2 = 5-hydroxy-4-imidazoleacetate + NAD+ + H2O
show the reaction diagram
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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
histidine metabolism
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Histidine metabolism
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SYSTEMATIC NAME
IUBMB Comments
4-imidazoleacetate,NADH:oxygen oxidoreductase (5-hydroxylating)
A flavoprotein (FAD).
CAS REGISTRY NUMBER
COMMENTARY hide
9029-65-6
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
4-imidazoleacetate + NAD(P)H + O2 + H+
5-hydroxy-4-imidazoleacetate + NAD(P)+ + H2O
show the reaction diagram
4-imidazoleacetate + NADH + O2
5-hydroxy-4-imidazoleacetate + NAD+ + H2O
show the reaction diagram
5-hydroxyindoleacetate + NAD(P)H + O2 + H+
? + NAD(P)+ + H2O
show the reaction diagram
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9.4% relative activity to 4-imidazoleacetate
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?
imidazolelactate + NADH + O2 + H+
5-hydroxyimidazolelactate + NAD+ + H2O
show the reaction diagram
imidazolepropionate + NAD(P)H + O2 + H+
5-hydroxyimidazolepropionate + NAD(P)+ + H2O
show the reaction diagram
imidazolepyruvate + O2 + NAD(P)H + H+
5-hydroxyimidazolepyruvate + NAD(P)+ + H2O
show the reaction diagram
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2.8% relative activity to 4-imidazoleacetate
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?
indoleacetate + NAD(P)H + O2 + H+
5-hydroxyindoleacetate + NAD(P)+ + H2O
show the reaction diagram
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7.3% relative activity to 4-imidazoleacetate
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?
N-methylimidazoleacetate + NAD(P)H + O2 + H+
5-hydroxy-N-methylimidazoleacetate + NAD(P)+ + H2O
show the reaction diagram
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7.6% relative activity to 4-imidazoleacetate
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?
sodium diethyldithiocarbamate + NADH + O2
? + NAD+ + H2O
show the reaction diagram
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-imidazoleacetate + NADH + O2
5-hydroxy-4-imidazoleacetate + NAD+ + H2O
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADPH
additional information
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the enzyme contains 2 mol of titratable suflhydryl groups, one of which is essential, possibly as a substrate-binding site, for the oxygenation of imidazoleacetate
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
5-hydroxyindoleacetate
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11% inhibition at 4.5 mM
dihydroxymandelate
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53% inhibition at 4.5 mM
Dihydroxyphenylacetate
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66% inhibition at 4.5 mM
ethyl-mercuric chloride
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homogentisate
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50% inhibition at 4.5 mM
homovanillic acid
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5% inhibition at 4.5 mM
Imidazolepyruvate
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56% inhibition at 4.5 mM
indoleacetate
m-hydroxyphenylacetate
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79% inhibition at 4.5 mM
Mercury compounds
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methyl-mercuric chloride
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N-methylimidazoleacetate
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11% inhibition at 4.5 mM
nicotinate
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65% inhibition at 20 mM
p-chloromercuribenzoate
p-hydroxybenzoate
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38% inhibition at 4.5 mM
p-hydroxyphenylacetate
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47% inhibition at 4.5 mM
phenyl-mercuric acetate
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phenylacetate
Silver compounds
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Sodium mersalyl
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vanillyl mandelic acid
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9% inhibition at 4.5 mM
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
23
5-hydroxyindoleacetate
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0.3 - 0.5
imidazoleacetate
64
indoleacetate
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44
N-methylimidazoleacetate
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0.002 - 0.03
NADH
0.02
O2
0.01
Sodium diethyldithiocarbamate
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polarographic method
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
37.7
imidazoleacetate
Pseudomonas sp.
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
87000 - 90000
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sedimentation equilibrium, gel filtration
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
20
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2% loss of activity, 0.1 M potassium phosphate, pH 7.2, 5 min
30
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50% loss of activity, 0.1 M potassium phosphate, pH 7.2, 5 min
40
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95% loss of activity, 0.1 M potassium phosphate, pH 7.2, 5 min
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°C, potassium phosphate buffer, pH 7.2, no loss of activity for at least 1 month
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-20°C, stable for at least 6 months
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4°C, 5-100 mM potassium phosphate buffer, pH 7.2, almost full activity retained for several days
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
partial, using ammonium sulfate precipitation and column chromatography on DEAE-Sephadex A-50
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using protamine sulfate treatment, ammonium sulfate fractionation, chromatography on TEAE-cellulose column, calcium phosphate gel treatment and chromatography on DEAE-Sephadex column
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