1.17.99.2: ethylbenzene hydroxylase

This is an abbreviated version!
For detailed information about ethylbenzene hydroxylase, go to the full flat file.

Word Map on EC 1.17.99.2

Reaction

ethylbenzene
+
H2O
+
acceptor
=
(S)-1-phenylethanol
+
reduced acceptor

Synonyms

ethylbenzene dehydrogenase, EBDH

ECTree

     1 Oxidoreductases
         1.17 Acting on CH or CH2 groups
             1.17.99 With unknown physiological acceptors
                1.17.99.2 ethylbenzene hydroxylase

Substrates Products

Substrates Products on EC 1.17.99.2 - ethylbenzene hydroxylase

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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(1S)-1-(4-ethylphenyl)ethanol + H2O + ferricenium
(1S,1'S)-1,1'-(benzene-1,4-diyl)diethanol + ferrocene
show the reaction diagram
-
-
-
-
?
1,2,3,4-tetrahydronaphthalene + H2O + ferricenium
(S)-1,2,3,4-tetrahydronaphthalen-1-ol + ferrocene
show the reaction diagram
-
-
-
-
?
1,2-diethylbenzene + H2O + ferricenium
(S)-1-(2-ethylphenyl)ethanol + ferrocene
show the reaction diagram
-
-
-
-
?
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
(S)-1-(4-ethylphenyl)ethanol + ferrocene
show the reaction diagram
-
-
-
-
?
1,4-diethylbenzene + H2O + ferricenium
1-(4-ethylphenyl)ethanol + 1,1'-(1,4-phenylene)diethanol + ferrocene
show the reaction diagram
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-2-methylbenzene + H2O + ferricenium
(S)-1-(2-methylphenyl)ethanol + ferrocene
show the reaction diagram
-
-
-
-
?
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
-
-
?
1-ethyl-3-methylbenzene + H2O + ferricenium
(S)-1-(3-methylphenyl)ethanol + ferrocene
show the reaction diagram
-
-
-
-
?
1-ethyl-4-fluorobenzene + H2O + ferricenium
(S)-1-(4-fluorophenyl)ethanol + ferrocene
show the reaction diagram
-
-
-
-
?
1-ethyl-4-methoxybenzene + H2O + ferricenium
(S)-1-(4-methoxyphenyl)ethanol + ferrocene
show the reaction diagram
-
-
-
-
?
1-ethyl-4-methylbenzene + H2O + acceptor
? + reduced acceptor
show the reaction diagram
-
28% of the activity with ethylbenzene
-
-
?
1-ethyl-4-methylbenzene + H2O + ferricenium
(S)-1-(4-methylphenyl)ethanol + ferrocene
show the reaction diagram
-
-
-
-
?
1H-indene + H2O + ferricenium
(S)-1H-inden-1-ol + ferrocene
show the reaction diagram
-
-
-
-
?
2,3-dihydro-1H-indene + H2O + ferricenium
(S)-2,3-dihydro-1H-inden-1-ol + ferrocene
show the reaction diagram
-
-
-
-
?
2-ethyl-1H-pyrrole + H2O + acceptor
? + reduced acceptor
show the reaction diagram
-
234.5% of the activity with ethylbenzene
-
-
?
2-ethyl-1H-pyrrole + H2O + ferricenium
(S)-1-(1H-pyrrol-2-yl)ethanol + ferrocene
show the reaction diagram
-
-
-
-
?
2-ethyl-aniline + H2O + acceptor
? + reduced acceptor
show the reaction diagram
-
94.5% of the activity with ethylbenzene
-
-
?
2-ethylaniline + H2O + acceptor
?
show the reaction diagram
2-ethylaniline + H2O + ferricenium
?
show the reaction diagram
2-ethylaniline + H2O + ferricenium
? + ferrocene
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
(S)-1-(furan-2-yl)ethanol + ferrocene
show the reaction diagram
-
-
-
-
?
2-ethylfuran + H2O + ferricenium
1-(2-furyl)ethanol + ferrocene
show the reaction diagram
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
-
-
?
2-ethylnaphthalene + H2O + ferricenium
(S)-1-(naphthalen-2-yl)ethanol + ferrocene
show the reaction diagram
-
-
-
-
?
2-ethylnaphthalene + H2O + ferricenium
? + ferrocene
show the reaction diagram
-
9.3% activity compared to ethylbenzene
-
-
?
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 + ferrocene
show the reaction diagram
-
55% activity compared to 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-ethylpyrrole + H2O + ferricenium
? + ferrocene
show the reaction diagram
-
228% activity compared to ethylbenzene
-
-
?
2-ethylthiophene + ferricyanide
(S)-1-(2-thienyl)-ethanol + ferrocyanide
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
(S)-1-(thiophen-2-yl)ethanol + ferrocene
show the reaction diagram
-
-
-
-
?
2-ethylthiophene + H2O + ferricenium
1-thien-2-ylethanol + ferrocene
show the reaction diagram
-
236% activity compared to 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 + reduced acceptor
show the reaction diagram
-
-
-
-
?
2-ethyltoluene + H2O + ferricenium
? + ferrocene
show the reaction diagram
-
3.8% activity compared to ethylbenzene
-
-
?
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
-
-
?
3-ethylphenol + H2O + ferricenium
3-(1-hydroxyethyl)phenol + ferrocene
show the reaction diagram
-
19% activity compared to ethylbenzene
-
-
?
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
-
-
?
3-ethylpyridine + H2O + ferricenium
?
show the reaction diagram
-
-
-
-
?
3-ethylpyridine + H2O + ferricenium
? + ferrocene
show the reaction diagram
-
16% activity compared to ethylbenzene
-
-
?
3-ethyltoluene + H2O + acceptor
1-(3-methylphenyl)ethanol + acceptor
show the reaction diagram
-
-
-
-
?
3-ethyltoluene + H2O + ferricenium
? + ferrocene
show the reaction diagram
-
10% activity compared to ethylbenzene
-
-
?
3-methyl-2-pentene + molybdopterin
?
show the reaction diagram
3-phenyl-1-propene + H2O + ferricyanide
? + ferrocyanide
show the reaction diagram
3-phenyl-1-propene + H2O + ferrocenium
? + ferrocene
show the reaction diagram
3-phenyl-1-propyne + H2O + ferricyanide
? + ferrocyanide
show the reaction diagram
3-phenyl-1-propyne + H2O + ferrocenium
? + ferrocene
show the reaction diagram
-
-
-
-
?
3-phenylprop-1-ene + H2O + ferricenium
(S)-1-phenylprop-2-en-1-ol + ferrocene
show the reaction diagram
-
-
-
-
?
3-phenylprop-1-yne + H2O + ferricenium
(S)-1-phenylprop-2-yn-1-ol + ferrocene
show the reaction diagram
-
-
-
-
?
4-bromoethylbenzene + H2O + acceptor
?
show the reaction diagram
-
-
-
-
?
4-chloroethylbenzene + H2O + acceptor
?
show the reaction diagram
-
-
-
-
?
4-cyanoethylbenzene + H2O + acceptor
?
show the reaction diagram
-
-
-
-
?
4-ethyl-1,1'-biphenyl + H2O + ferricenium
(S)-1-([1,1'-biphenyl]-4-yl)ethanol + (R)-1-([1,1'-biphenyl]-4-yl)ethanol + ferrocene
show the reaction diagram
-
-
-
-
?
4-ethyl-N,N-dimethylaniline + H2O + acceptor
?
show the reaction diagram
-
-
-
-
?
4-ethylaniline + H2O + acceptor
?
show the reaction diagram
-
-
-
-
?
4-ethylaniline + H2O + ferricenium
? + ferrocene
show the reaction diagram
-
130% activity compared to ethylbenzene
-
-
?
4-ethylanisole + H2O + acceptor
1-(4-methoxyphenyl)ethanol + acceptor
show the reaction diagram
-
-
-
-
?
4-ethylanisole + H2O + ferricenium
1-(4-methoxyphenyl)ethanol + ferrocene
show the reaction diagram
-
22% activity compared to ethylbenzene
-
-
?
4-ethylanisole + H2O + ferricenium
1-(4-methoxyphenyl)ethanol + ferrocenium
show the reaction diagram
-
-
-
-
?
4-ethylbiphenyl + ferricenium + H2O
1-(1,1'-biphenyl-4-yl)ethanol + ferrocene
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-ethylbiphenyl + H2O + ferricenium
? + ferrocene
show the reaction diagram
-
30% activity compared to ethylbenzene
-
-
?
4-ethylphenol + ferricenium
?
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
-
-
?
4-ethylphenol + H2O + ferricenium
4-(1-hydroxyethyl)phenol + ferrocene
show the reaction diagram
-
251% activity compared to ethylbenzene
-
-
?
4-ethylphenol + H2O + ferricenium
4-(1-hydroxyethyl)phenol + ferrocenium
show the reaction diagram
-
best substrate
-
-
?
4-ethylpyridine + H2O + acceptor
?
show the reaction diagram
-
substrate shows 50fold decreased activities of hydroxylation, relative specific activity: 2%
-
-
?
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 + ferrocene
show the reaction diagram
-
28% activity compared to ethylbenzene
-
-
?
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-fluoroethylbenzene + H2O + ferricenium
? + ferrocene
show the reaction diagram
-
15% activity compared to ethylbenzene
-
-
?
4-propylphenol + H2O + acceptor
4-(1-hydroxypropyl)phenol + acceptor
show the reaction diagram
-
-
-
-
?
4-propylphenol + H2O + ferricenium
4-(1-hydroxypropyl)phenol + ferrocene
show the reaction diagram
-
175% activity compared to ethylbenzene
-
-
?
4-propylphenol + H2O + ferricenium
4-(1-hydroxypropyl)phenol + ferrocenium
show the reaction diagram
-
-
-
-
?
5-methoxy-2,3-dihydro-1H-indene + H2O + ferricenium
(S)-5-methoxy-2,3-dihydro-1H-inden-1-ol + (S)-6-methoxy-2,3-dihydro-1H-inden-1-ol + ferrocene
show the reaction diagram
-
-
-
-
?
allylbenzene + ferricenium
?
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%
-
-
?
ethylbenzene + H2O + acceptor
(S)-1-phenylethanol + reduced acceptor
show the reaction diagram
ethylbenzene + H2O + ferricenium
(S)-1-phenylethanol + ferrocene
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
-
-
?
ethylbenzene + H2O + ferricyanide
(S)-1-phenylethanol + ferrocyanide
show the reaction diagram
-
-
-
-
?
ethylbenzene + H2O + ferrocenium
(S)-1-phenylethanol + ferrocene
show the reaction diagram
-
-
-
-
?
ethylbenzene + H2O + molybdopterin
(S)-1-phenylethanol + molybdopterin (reduced form)
show the reaction diagram
ethylbenzene + H2O + phenazine methosulfate
(S)-1-phenylethanol + reduced phenazine methosulfate
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 + ferricenium
1-phenylpropanol + ferrocene
show the reaction diagram
-
14% activity compared to ethylbenzene
-
-
?
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-phenylpropan-1-ol + ferrocene
show the reaction diagram
-
-
-
-
?
propylbenzene + H2O + ferricenium
(S)-1-phenylpropanol + ferrocene
show the reaction diagram
propylbenzene + H2O + ferricenium
(S)-1-phenylpropanol + ferrocenium
show the reaction diagram
-
-
-
-
?
rac-1-(4-ethylphenyl)ethanol + H2O + ferricenium
(1S)-1,1'-(benzene-1,4-diyl)diethanol + ferrocene
show the reaction diagram
-
-
-
-
?
additional information
?
-