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(10R)-hydroxy-(11S,12S)-epoxy-(5Z,8Z,14Z)-eicosatrienoic acid + H2O
(10R,11R,12S)-trihydroxy-(5Z,8Z,14Z)-eicosatrienoic acid
(11S,12S)-epoxy-5,14-cis-7,9-trans-eicosatetraenoic acid + H2O
(11R,12S)-dihydroxy-5,14-cis-7,9-trans-eicosatetraenoic acid + H2O
-
i.e. 11,12-leukotriene A4
-
?
(12Z)-9,10-epoxyoctadec-12-enoic acid
(12Z)-9,10-dihydroxyoctadec-12-enoic acid
-
-
-
?
(1S,2S)-beta-methylstyrene oxide + H2O
?
enzyme attacks almost exclusively at the benzylic position
-
-
?
(1S,2S)-trans-methylstyrene oxide + H2O
?
a hydrogen bond from Tyr465 to the substrate oxygen is essential for controlling the regioselectivity of the reaction
-
-
r
(3-phenyl-oxiranyl)-acetic acid cyano-(6-methoxy-naphthalen-2-yl)-methyl ester + H2O
6-methoxy-2-naphthaldehyde + ?
-
substrate for high-throughput screen
product is fluorescent
-
?
(3-phenyl-oxiranyl)-acetic acid cyano-(6-methoxy-naphthalen-2-yl)-methyl ester + H2O
?
-
-
-
-
?
(3-phenyl-oxiranyl)-acetic acid cyano-(6-methoxynaphthalen-2-yl)-methyl ester + H2O
6-methoxy-2-naphthaldehyde + ?
-
-
-
-
?
(5Z,11Z,14Z)-8,9-epoxyeicosa-5,11,14-trienoic acid + H2O
(5Z,11Z,14Z)-8,9-dihydroxyeicosa-5,11,14-trienoic acid
(5Z,11Z,14Z)-8,9-epoxyeicosa-8,11,14-trienoic acid + H2O
(5Z,11Z,14Z)-8,9-dihydroxyeicosa-5,11,14-trienoic acid
-
-
-
?
(5Z,11Z,14Z)-8,9-epoxyeicosatrienoic acid + H2O
(5Z,11Z,14Z)-8,9-dihydroxyeicosatrienoic acid
(5Z,8Z)-N-((2-methoxy-4-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenyl)sulfonyl)-10-(3-((Z)-oct-2-en-1-yl)oxiran-2-yl)deca-5,8-dienamide + H2O
?
-
-
-
?
(5Z,8Z,11Z)-14,15-epoxyeicosa-5,8,11-trienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosa-5,8,11-trienoic acid
(5Z,8Z,11Z)-14,15-epoxyeicosatrienoic acid + H2O
(5Z,8Z,11Z)-14,15-dihydroxyeicosatrienoic acid
(5Z,8Z,11Z)-N-((2-methoxy-4-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenyl) sulfonyl)-13-(3-pentyloxiran-2-yl)trideca-5,8,11-trienamide + H2O
?
-
-
-
?
(5Z,8Z,11Z,14R,15S)-14,15-epoxyeicosa-5,8,11-trienoic acid + H2O
(5Z,8Z,11Z,14R,15R)-14,15-dihydroxyeicosa-5,8,11-trienoic acid + (5Z,8Z,11Z,14S,15S)-14,15-dihydroxyeicosa-5,8,11-trienoic acid
-
-
-
-
?
(5Z,8Z,11Z,14S,15R)-14,15-epoxyeicosa-5,8,11-trienoic acid + H2O
(5Z,8Z,11Z,14R,15R)-14,15-dihydroxyeicosa-5,8,11-trienoic acid + (5Z,8Z,11Z,14S,15S)-14,15-dihydroxyeicosa-5,8,11-trienoic acid
-
-
-
-
?
(5Z,8Z,14Z)-11,12-epoxyeicosa-5,8,14-trienoic acid + H2O
(5Z,8Z,14Z)-11,12-dihydroxyeicosa-5,8,14-trienoic acid
(5Z,8Z,14Z)-11,12-epoxyeicosatrienoic acid + H2O
(5Z,8Z,14Z)-11,12-dihydroxyeicosatrienoic acid
(8R)-hydroxy-(11S,12S)-epoxy-(5Z,9E,14Z)-eicosatrienoic acid + H2O
(8R,11R,12S)-trihydroxy-(5Z,9E,14Z)-eicosatrienoic acid
(8Z,11Z,14Z)-5,6-epoxyeicosa-8,11,14-trienoic acid + H2O
(8Z,11Z,14Z)-5,6-dihydroxyeicosa-8,11,14-trienoic acid
(8Z,11Z,14Z)-5,6-epoxyeicosatrienoic acid + H2O
(8Z,11Z,14Z)-5,6-dihydroxyeicosatrienoic acid
(9Z)-12,13-epoxyoctadec-9-enoic acid + H2O
(9Z)-12,13-dihydroxyoctadec-9-enoic acid
-
-
-
?
(9Z)-12,13-epoxyoctadecenoic acid + H2O
(9Z)-12,13-dihydroxyoctadecenoic acid
(R)-1-chloro-2-(2,4-difluorophenyl)-2,3-epoxypropane + H2O
(R)-3-chloro-2-(2,4-difluoro-phenyl)-propane-1,2-diol
-
in a racemic mixture only the (R)-enantiomeric epoxide is converted to the (R)-enantiomeric diol
-
-
?
(R)-4-nitrostyrene oxide + H2O
?
(R)-glycidyl phenyl ether + H2O
?
(R)-p-nitrostyrene oxide + H2O
1-(4-nitrophenyl)ethane-1,2-diol
(R)-styrene oxide + H2O
(R)-styrene glycol
(R)-styrene oxide + H2O
1-phenylethane-1,2-diol
(R,S)-4-nitrostyrene oxide + H2O
1-(4-nitrophenyl)ethane-1,2-diol
-
-
-
-
?
(S)-4-nitrostyrene oxide
1-(4-nitrophenyl)ethane-1,2-diol
-
-
-
-
?
(S)-p-nitrostyrene oxide + H2O
1-(4-nitrophenyl)ethane-1,2-diol
(S)-styrene oxide + H2O
(S)-phenyl-1,2-ethanediol
wild-type and mutant enzymes prefer the S-enantiomer, enantioselective hydrolytic activity of sEH
-
-
?
(S)-styrene oxide + H2O
(S)-styrene glycol
(S)-styrene oxide + H2O
1-phenylethane-1,2-diol
preferred attack at the benzylic position
-
-
?
(S)-styrene oxide + H2O
?
1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,41,5,6,7,8,8a-octahydro-1,4-methanonaphthalene + H2O
?
1,3-trans-diphenylpropene oxide + H2O
1,3-diphenylpropane-1,2-diol
1-myristoyl-sn-glycerol 3-phosphate + H2O
?
-
-
-
?
11,12-epoxy-eicosatrienoic acid + H2O
11,12-dihydroxy-eicosatrienoic acid
-
-
-
?
11,12-epoxyeicosatrienoic acid + H2O
11,12-dihydroxyeicosatrienoic acid
11,12-leukotriene A4 + H2O
?
-
-
-
-
?
11R,12S-epoxyeicosatrienoic acid + H2O
11R,12S-dihydroxyeicosatrienoic acid
-
-
-
?
11S,12R-epoxyeicosatrienoic acid + H2O
11S,12R-hydroxyeicosatrienoic acid
-
-
-
?
12,13-cis-epoxy-octadeca-9E-enoic acid + H2O
?
-
-
-
?
12,13-epoxy octadeca-(9Z)-eneoic acid + H2O
?
12,13-trans-epoxy-octadeca-9E-enoic acid + H2O
?
-
-
-
?
12-phosphonooxyoctadec-9E-enoic acid + H2O
(9E)-octadecenoic acid + phosphate
-
-
-
-
?
12-phosphonooxyoctadec-9Z-enoic acid + H2O
(9Z)-octadecenoic acid + phosphate
-
-
-
-
?
12-phosphonooxyoctadecanoic acid + H2O
octadecanoic acid + phosphate
-
-
-
-
?
14,15-epoxy-(5Z,8Z,11Z)-eicosatrienoic acid + H2O
14,15-dihydroxyeicosatrienoic acid
-
-
-
?
14,15-epoxyeicosatrienoic acid + H2O
14,15-dihydroxyeicosatrienoic acid
14,15-leukotriene A4 + H2O
?
-
-
-
-
?
14R,15S-epoxyeicosatrienoic acid + H2O
14R,15S-dihydroxyeicosatrienoic acid
-
-
-
?
14S,15R-epoxy-eicosatrienoic acid + H2O
14S,15R-dihydroxy-eicosatrienoic acid
-
-
-
?
14S,15R-epoxyeicosatrienoic acid + H2O
14S,15R-dihydroxyeicosatrienoic acid
-
-
-
?
14S,15S-trans-epoxy-(5Z,8Z,10E,12E)-eicosatetraenoic acid + H2O
14S,15R-dihydroxy-(5Z,8Z,10E,12E)-eicosatetraenoic acid
-
-
-
?
2,2-dimethylstyrene oxide + H2O
?
-
-
-
-
?
2,3-epoxy-1,3-diphenyl-propane + H2O
?
2,3-squalene oxide + H2O
?
2-acetylaminofluorene + H2O
?
2-methyl styrene oxide + H2O
(2R)-2-phenylpropane-1,2-diol
-
-
highly enantioselective in ionic liquid [bmim][PF6]in presence of 10% water
-
?
2-methylphenyl glycidyl ether + H2O
?
3-phenyl-cyano(6-methoxy-2-naphthalenyl)methyl ester 2-oxiraneacetic acid + H2O
6-methoxy-2-naphthaldehyde + ?
-
-
-
-
?
3-phenyl-cyano(6-methoxy-2-naphthalenyl)methyl ester-2-oxiraneacetic acid + H2O
6-methoxy-2-naphtaldehyde + ?
-
-
-
?
3-phenyl-cyano(6-methoxy-2-naphthalenyl)methyl ester-2-oxiraneacetic acid + H2O
6-methoxy-2-naphthaldehyde + ?
fluorometric activity assay substrate
-
-
?
3-phenyl-cyano(6-methoxy-2-naphthalenyl)methyl ester-2-oxiraneacetic acid + H2O
6-methoxynaphthaldehyde + ?
-
-
-
-
?
3-phenyl-cyano(6-methoxy-2-naphthalenyl)methyl ester-2-oxiraneacetic acid + H2O
?
-
-
-
?
3-phenyl-cyano-(6-methoxy-2-naphthalenyl)methylester-2-oxirane-acetic acid + H2O
6-methoxynaphtaldehyde + ?
the non-fluorescent substrate can be hydrolyzed by enzyme sEH to the fluorescent 6-methoxynaphtaldehyde
-
-
?
3-phenyl-oxiranyl-acetic acid cyano-(6-methoxy-naphthalen-2-yl)-methyl ester + H2O
?
-
-
-
-
?
3-phenylcyano-(6-methoxy-2-naphthalenyl)methyl ester 2-oxiraneacetic acid + H2O
?
-
-
-
?
4-chlorostyrene oxide + H2O
(1R)-1-(4-chlorophenyl)ethane-1,2-diol
-
-
conversion of racemic substrate via attack of the benzylic position to R-diol with 96% enantiomeric excess
-
?
4-methylphenylglycidyl ether + H2O
?
4-nitrophenyl (2R,3R)-2,3-epoxy-3-(4-nitrophenyl)propyl carbonate + H2O
?
-
-
-
-
?
4-nitrophenyl (2R,3R)-2,3-epoxy-3-phenylpropyl carbonate + H2O
?
4-nitrophenyl (2S,3S)-2,3-epoxy-3-(4-nitrophenyl)propyl carbonate + H2O
?
-
preferred phenylpropyl carbonate substrate
-
-
?
4-nitrophenyl (2S,3S)-2,3-epoxy-3-phenylpropyl carbonate + H2O
?
-
-
-
-
?
4-nitrophenyl [(2R,3R)-3-phenyloxiran-2-yl]methyl carbonate + H2O
?
-
15.2% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
4-nitrophenyl [(2S,3S)-3-phenyloxiran-2-yl]methyl carbonate + H2O
?
-
38% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
4-nitrophenyl-trans-2,3-epoxy-3-phenylpropyl carbonate + H2O
?
4-nitrostyrene 7,8-oxide + H2O
?
4-nitrostyrene oxide + H2O
(1R)-1-(4-nitrophenyl)ethane-1,2-diol
-
-
conversion of racemic substrate via attack of the benzylic position to R-diol with 80% enantiomeric excess
-
?
4-nitrostyrene oxide + H2O
?
4-t-butylstyrene oxide + H2O
(1R)-1-(4-t-butylphenyl)ethane-1,2-diol
-
-
highly enantioselective in ionic liquid [bmim][PF6]in presence of 10% water
-
?
5,6-epoxyeicosatrienoic acid + H2O
5,6-dihydroxyeicosatrienoic acid
5,6-epoxyeicosatrienoic acid + H2O
5,6-hydroxyeicosatrienoic acid
5,6-leukotriene A4 + H2O
?
-
-
-
-
?
5alpha-cholest-2-ene beta-oxide + H2O
?
-
-
-
-
?
6,8-difluoro-4-methylumbelliferyl trans-2,3-epoxy-3-phenylpropylcarbonate + H2O
?
-
-
-
?
8,9-epoxyeicosatrienoic acid + H2O
8,9-dihydroxyeicosatrienoic acid
8,9-epoxyeicosatrienoic acid + H2O
8,9-hydroxyeicosatrienoic acid
-
-
-
-
?
8R,9S-epoxyeicosatrienoic acid + H2O
8R,9S-dihydroxyeicosatrienoic acid
-
-
-
?
8S,9R-epoxyeicosatrienoic acid + H2O
8S,9R-dihydroxyeicosatrienoic acid
-
-
-
?
9(10),12(13)-diepoxyoctadecanoic acid + H2O
9,10,12,13-tetrahydroxyoctadecanoic acid
-
-
-
?
9,10-epoxy octadeca-(12Z)-eneoic acid + H2O
?
9,10-epoxy-18-hydroxy octadeca-(12Z)-eneoic acid + H2O
?
9-hydroxy-10,11-epoxy octadeca-(12Z)-eneoic acid + H2O
?
9R,10R-trans-epoxy-13R-hydroxy-11E-octadecenoic acid + H2O
(9R,10S,13R)-trihydroxy-11E-octadecenoic acid
9R,10S-cis-epoxy-13R-hydroxy-11E-octadecenoic acid
(9R,10R,13R)-trihydroxy-11E-octadecenoic acid
-
-
-
?
9R,10S-cis-epoxy-13R-hydroxy-11E-octadecenoic acid + H2O
(9R,10R,13R)-trihydroxy-11E-octadecenoic acid
-
-
-
?
alpha-cyanocarbonate epoxide + H2O
?
arachidonic acid 11,12-oxide + H2O
11,12-dihydroxyarachidonic acid
-
-
-
-
?
arachidonic acid 14,15-oxide + H2O
14,15-dihydroxyarachidonic acid
-
-
-
-
?
arachidonic acid 5,6-oxide + H2O
5,6-dihydroxyarachidonic acid
-
-
-
-
?
arachidonic acid 8,9-oxide + H2O
8,9-dihydroxyarachidonic acid
-
-
-
-
?
benzopyrene 4,5-oxide + H2O
(-)benzopyrene 4,5-dihydrodiol
cholesterol 5,6-alpha-oxide + H2O
?
-
very weak activity
-
-
?
cis-(9R,10S)-epoxystearic acid + H2O
threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid
-
-
enantioselective, low production rate of the (9R,10R)-diol by wild-type and E404D mutant
-
?
cis-(9S,10R)-epoxystearic acid + H2O
threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid
-
-
enantioselective, low production rate of the (9R,10R)-diol by wild-type and E404D mutant
-
?
cis-1,2-dimethylstyrene oxide + H2O
?
-
-
-
-
?
cis-1,3-diphenylpropene oxide + H2O
1,3-diphenylpropane-1,2-diol
cis-1,3-diphenylpropene oxide + H2O
?
cis-11,12-epoxyeicosatrienoic acid + H2O
?
-
-
-
-
?
cis-11,12-epoxyeicosatrienoic acid + H2O
cis-11,12-dihydroxyeicosatrienoic acid
-
-
-
?
cis-14,15-epoxyeicosatrienoic acid + H2O
?
cis-14,15-epoxyeicosatrienoic acid + H2O
cis-14,15-dihydroxyeicosatrienoic acid
cis-2-methylstyrene oxide + H2O
?
-
-
-
-
?
cis-8,9-epoxyeicosatrienoic acid + H2O
?
-
-
-
-
?
cis-8,9-epoxyeicosatrienoic acid + H2O
cis-8,9-dihydroxyeicosatrienoic acid
-
-
-
?
cis-8-ethylstyrene 7,8-oxide + H2O
?
cis-9,10-epoxy-12-octadecenoate methyl ester + H2O
9,10-dihydroxystearic acid methyl ester
cis-9,10-epoxy-12-octadecenoate methyl ester + H2O
?
-
5.2% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
cis-9,10-epoxystearate + H2O
threo-9,10-dihydroxystearate
-
-
-
?
cis-9,10-epoxystearic acid + H2O
9,10-dihydroxystearic acid
cis-9,10-epoxystearic acid + H2O
?
-
7.9% of the activity with 2,3-epoxy-1,3-diphenyl-propane
-
-
?
cis-stilbene oxide + H2O
(1R,2R)-1,2-diphenylethane-1,2-diol
cis-stilbene oxide + H2O
1,2-diphenylethane-1,2-diol
cis-stilbene oxide + H2O
?