Information on EC 1.17.99.2 - ethylbenzene hydroxylase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.17.99.2
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RECOMMENDED NAME
GeneOntology No.
ethylbenzene hydroxylase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
ethylbenzene + H2O + acceptor = (S)-1-phenylethanol + reduced acceptor
show the reaction diagram
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
Ethylbenzene degradation
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ethylbenzene degradation (anaerobic)
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Metabolic pathways
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Microbial metabolism in diverse environments
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SYSTEMATIC NAME
IUBMB Comments
ethylbenzene:acceptor oxidoreductase
Involved in the anaerobic catabolism of ethylbenzene by denitrifying bacteria. Ethylbenzene is the preferred substrate; the enzyme from some strains oxidizes propylbenzene, 1-ethyl-4-fluorobenzene, 3-methylpent-2-ene and ethylidenecyclohexane. Toluene is not oxidized. p-Benzoquinone or ferrocenium can act as electron acceptor. Contains molybdopterin, [4Fe-4S] clusters and heme b.
CAS REGISTRY NUMBER
COMMENTARY hide
249614-72-0
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
EB1
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
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EBDH is a bacterial molybdopterin enzyme capable of stereospecific anaerobic hydroxylation of alkylaromatic compounds to secondary alcohols. It is a key biocatalyst in the metabolism of ethylbenzene-degrading bacteria such as Aromatoleum aromaticum, which converts ethylbenzene to (S)-1-phenylethanol
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
1,4-diethylbenzene + H2O + acceptor
1-(4-ethylphenyl)ethanol + 1,1'-(1,4-phenylene)diethanol + acceptor
show the reaction diagram
1,4-diethylbenzene + H2O + acceptor
? + reduced acceptor
show the reaction diagram
-
35% of the activity with ethylbenzene
-
-
?
1,4-diethylbenzene + H2O + ferricenium
1-(4-ethylphenyl)ethanol + 1,1'-(1,4-phenylene)diethanol + ferrocenium
show the reaction diagram
1-ethyl-2-methylbenzene + H2O + acceptor
? + reduced acceptor
show the reaction diagram
-
3.8% of the activity with ethylbenzene
-
-
?
1-ethyl-3-fluorobenzene + H2O + acceptor
? + reduced acceptor
show the reaction diagram
-
15% of the activity with ethylbenzene
-
-
?
1-ethyl-3-methylbenzene + H2O + acceptor
? + reduced acceptor
show the reaction diagram
-
10% of the activity with ethylbenzene
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-
?
1-ethyl-4-methylbenzene + H2O + acceptor
? + reduced acceptor
show the reaction diagram
-
28% of the activity with ethylbenzene
-
-
?
2-ethyl-1H-pyrrole + H2O + acceptor
? + reduced acceptor
show the reaction diagram
-
234.5% of the activity with ethylbenzene
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-
?
2-ethyl-aniline + H2O + acceptor
? + reduced acceptor
show the reaction diagram
-
94.5% of the activity with ethylbenzene
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-
?
2-ethylaniline + H2O + acceptor
?
show the reaction diagram
2-ethylaniline + H2O + ferricenium
?
show the reaction diagram
2-ethylfuran + H2O + acceptor
?
show the reaction diagram
2-ethylfuran + H2O + acceptor
? + reduced acceptor
show the reaction diagram
-
133.9% of the activity with ethylbenzene
-
-
?
2-ethylfuran + H2O + ferricenium
1-(2-furyl)ethanol + ferrocenium
show the reaction diagram
-
-
-
-
?
2-ethylfuran + H2O + ferricenium
?
show the reaction diagram
-
-
-
-
?
2-ethylnaphthalene + H2O + acceptor
?
show the reaction diagram
-
-
-
-
?
2-ethylnaphthalene + H2O + acceptor
? + reduced acceptor
show the reaction diagram
-
9.3% of the activity with ethylbenzene
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?
2-ethylphenol + H2O + acceptor
2-(1-hydroxyethyl)phenol + reduced acceptor
show the reaction diagram
-
-
-
-
?
2-ethylphenol + H2O + acceptor
? + reduced acceptor
show the reaction diagram
-
56.7% of the activity with ethylbenzene
-
-
?
2-ethylphenol + H2O + ferricenium
2-(1-hydroxyethyl)phenol + ferrocenium
show the reaction diagram
-
-
-
-
?
2-ethylpyrrole + H2O + acceptor
?
show the reaction diagram
-
-
-
-
?
2-ethylpyrrole + H2O + ferricenium
?
show the reaction diagram
-
-
-
-
?
2-ethylthiophene + H2O + acceptor
?
show the reaction diagram
-
-
-
-
?
2-ethylthiophene + H2O + acceptor
? + reduced acceptor
show the reaction diagram
-
242.9% of the activity with ethylbenzene
-
-
?
2-ethylthiophene + H2O + ferricenium
1-thien-2-ylethanol + ferrocenium
show the reaction diagram
-
-
-
-
?
2-ethylthiophene + H2O + ferricenium
?
show the reaction diagram
-
-
-
-
?
2-ethyltoluene + H2O + acceptor
1-(2-methylphenyl)ethanol + acceptor
show the reaction diagram
-
-
-
-
?
2-ethyltoluene + H2O + acceptor
1-(2-methylphenyl)ethanol + reduced acceptor
show the reaction diagram
-
-
-
-
?
3-ethylanisole + H2O + acceptor
1-(3-methoxyphenyl)ethanol + acceptor
show the reaction diagram
-
-
-
-
?
3-ethylphenol + H2O + acceptor
3-(1-hydroxyethyl)phenol + acceptor
show the reaction diagram
-
-
-
-
?
3-ethylphenol + H2O + acceptor
? + reduced acceptor
show the reaction diagram
-
24.3% of the activity with ethylbenzene
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-
?
3-ethylphenol + H2O + ferricenium
3-(1-hydroxyethyl)phenol + ferrocenium
show the reaction diagram
-
-
-
-
?
3-ethylpyridine + H2O + acceptor
?
show the reaction diagram
-
-
-
-
?
3-ethylpyridine + H2O + acceptor
? + reduced acceptor
show the reaction diagram
-
16.9% of the activity with ethylbenzene
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?
3-ethylpyridine + H2O + ferricenium
?
show the reaction diagram
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-
-
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?
3-ethyltoluene + H2O + acceptor
1-(3-methylphenyl)ethanol + acceptor
show the reaction diagram
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-
-
-
?
3-methyl-2-pentene + molybdopterin
?
show the reaction diagram
4-bromoethylbenzene + H2O + acceptor
?
show the reaction diagram
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-
-
-
?
4-chloroethylbenzene + H2O + acceptor
?
show the reaction diagram
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-
-
-
?
4-cyanoethylbenzene + H2O + acceptor
?
show the reaction diagram
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-
-
-
?
4-ethyl-N,N-dimethylaniline + H2O + acceptor
?
show the reaction diagram
-
-
-
-
?
4-ethylaniline + H2O + acceptor
?
show the reaction diagram
-
-
-
-
?
4-ethylanisole + H2O + acceptor
1-(4-methoxyphenyl)ethanol + acceptor
show the reaction diagram
-
-
-
-
?
4-ethylanisole + H2O + ferricenium
1-(4-methoxyphenyl)ethanol + ferrocenium
show the reaction diagram
-
-
-
-
?
4-ethylbiphenyl + H2O + acceptor
1-(1,1'-biphenyl-4-yl)ethanol + reduced acceptor
show the reaction diagram
4-ethylbiphenyl + H2O + ferricenium
1-(1,1'-biphenyl-4-yl)ethanol + reduced ferrocenium
show the reaction diagram
4-ethylphenol + H2O + acceptor
4-(1-hydroxyethyl)phenol + acceptor
show the reaction diagram
4-ethylphenol + H2O + acceptor
? + reduced acceptor
show the reaction diagram
-
259% of the activity with ethylbenzene
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-
?
4-ethylphenol + H2O + ferricenium
4-(1-hydroxyethyl)phenol + ferrocenium
show the reaction diagram
-
best substrate
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?
4-ethylpyridine + H2O + acceptor
?
show the reaction diagram
-
substrate shows 50fold decreased activities of hydroxylation, relative specific activity: 2%
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-
?
4-ethylresorcinol + H2O + acceptor
?
show the reaction diagram
-
-
-
-
?
4-ethyltoluene + H2O + acceptor
1-(4-methylphenyl)ethanol + acceptor
show the reaction diagram
-
-
-
-
?
4-ethyltoluene + H2O + ferricenium
1-(4-methylphenyl)ethanol + ferrocenium
show the reaction diagram
-
-
-
-
?
4-fluoro-ethylbenzene + molybdopterin
?
show the reaction diagram
4-fluoroethylbenzene + H2O + acceptor
?
show the reaction diagram
-
-
-
-
?
4-propylphenol + H2O + acceptor
4-(1-hydroxypropyl)phenol + acceptor
show the reaction diagram
-
-
-
-
?
4-propylphenol + H2O + ferricenium
4-(1-hydroxypropyl)phenol + ferrocenium
show the reaction diagram
-
-
-
-
?
allylbenzene + H2O + acceptor
?
show the reaction diagram
-
allylbenzene is hydroxylated 2.8fold faster than ethylbenzene. The introduced CH=CH2 group of the allyl chain may exert both steric and electronic effects on the energetic profile of the reaction. Relative specific activity: 281%
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-
?
ethylbenzene + H2O + acceptor
(S)-1-phenylethanol + reduced acceptor
show the reaction diagram
ethylbenzene + H2O + ferricenium
(S)-1-phenylethanol + ferrocenium
show the reaction diagram
-
EBDH catalyzes the oxygen-independent, stereospecific hydroxylation of ethylbenzene to (S)-1-phenylethanol, the direct anaerobic oxidation of a nonactivated hydrocarbon
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-
?
ethylbenzene + H2O + molybdopterin
(S)-1-phenylethanol + molybdopterin (reduced form)
show the reaction diagram
ethylbenzene + H2O + [Fe(III) (C5H5)2]+
(S)-1-phenylethanol + [Fe(II) (C5H5)2]
show the reaction diagram
ethylidenecyclohexane + H2O + ferricenium
?
show the reaction diagram
-
-
-
-
?
ethylidenecyclohexane + molybdopterin
?
show the reaction diagram
n-propylbenzene + H2O + acceptor
?
show the reaction diagram
-
-
-
-
?
n-propylbenzene + H2O + [Fe(III) (C5H5)2]+
(S)-1-phenylpropanol + [Fe(II) (C5H5)2]
show the reaction diagram
propylbenzene + H2O + acceptor
? + reduced acceptor
show the reaction diagram
-
15% of the activity with ethylbenzene
-
-
?
propylbenzene + H2O + ferricenium
(S)-1-phenylpropanol + ferrocenium
show the reaction diagram
-
-
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?
additional information
?
-
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
ethylbenzene + H2O + acceptor
(S)-1-phenylethanol + reduced acceptor
show the reaction diagram
additional information
?
-
-
EBDH is a bacterial molybdopterin enzyme capable of stereospecific anaerobic hydroxylation of alkylaromatic compounds to secondary alcohols
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-
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
heme
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a molybdenum/iron-sulfur/heme protein
iron-sulfur centre
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Molybdenum
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molybdenum cofactor
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molybdopterin
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Fe2+
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a molybdenum/iron-sulfur/heme protein
iron sulfur cluster
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located in beta-subunit
iron-sulfur centre
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-
Molybdenum
[Fe(III) (C5H5)2]+
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-
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
B-ethyl-1,2-azaborine
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N-ethyl-1,2-azaborine
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0243
2-ethylaniline
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pH 7.5, 30°C
0.0247
2-ethylfuran
-
pH 7.5, 30°C
0.0052
2-Ethylphenol
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pH 7.5, 30°C
0.0023
2-ethylpyrrole
-
pH 7.5, 30°C
0.0665
2-ethylthiophene
-
pH 7.5, 30°C
0.0093
3-Ethylphenol
-
pH 7.5, 30°C
0.0018
3-ethylpyridine
-
pH 7.5, 30°C
0.004 - 0.0405
4-Ethylphenol
0.003
allylbenzene
-
pH 7.5, 30°C
0.00045 - 0.045
ethylbenzene
0.0283
ferricenium
-
pH 7.5, 30°C
additional information
additional information
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
additional information
Azoarcus sp.
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relative kcat values
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.1
B-ethyl-1,2-azaborine
Aromatoleum aromaticum
-
pH and temperature not specified in the publication
0.0028
N-ethyl-1,2-azaborine
Aromatoleum aromaticum
-
pH and temperature not specified in the publication
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0035
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activity towards n-propylbenzene of cell extract from cells grown on ethylbenzene
0.0224
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activity towards ethylbenzene of cell extract from cells grown on ethylbenzene
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.5 - 9
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about maximum activity at both pH
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
PDB
SCOP
CATH
ORGANISM
UNIPROT
Aromatoleum aromaticum (strain EbN1)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
23000
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alpha,beta,gamma 1 * 96000 + 1 * 43000 + 1 * 23000, SDS-PAGE
23061
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alpha,beta,gamma 1 * 100000 + 1 * 35000 + 1 * 25000, SDS-PAGE, 1 * 104226 + 1 * 39643 + 1 * 23061, calculated from DNA-sequence
25000
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alpha,beta,gamma 1 * 100000 + 1 * 35000 + 1 * 25000, SDS-PAGE, 1 * 104226 + 1 * 39643 + 1 * 23061, calculated from DNA-sequence
35000
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alpha,beta,gamma 1 * 100000 + 1 * 35000 + 1 * 25000, SDS-PAGE, 1 * 104226 + 1 * 39643 + 1 * 23061, calculated from DNA-sequence
39643
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alpha,beta,gamma 1 * 100000 + 1 * 35000 + 1 * 25000, SDS-PAGE, 1 * 104226 + 1 * 39643 + 1 * 23061, calculated from DNA-sequence
43000
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alpha,beta,gamma 1 * 96000 + 1 * 43000 + 1 * 23000, SDS-PAGE
70000
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gel filtration of purified enzyme
96000
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alpha,beta,gamma 1 * 96000 + 1 * 43000 + 1 * 23000, SDS-PAGE
100000
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alpha,beta,gamma 1 * 100000 + 1 * 35000 + 1 * 25000, SDS-PAGE, 1 * 104226 + 1 * 39643 + 1 * 23061, calculated from DNA-sequence
104226
-
alpha,beta,gamma 1 * 100000 + 1 * 35000 + 1 * 25000, SDS-PAGE, 1 * 104226 + 1 * 39643 + 1 * 23061, calculated from DNA-sequence
155000
160000
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calculated from DNA-sequence
545000
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native PAGE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
trimer
additional information
OXIDATION STABILITY
ORGANISM
UNIPROT
LITERATURE
the enzyme is quickly inactivated in air in its reduced state
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685172
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
DNA microarray
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in Escherichia coli DH5alpha
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
biotechnology
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application of artificial neural networks for prediction of reaction kinetics