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1-(4-methoxyphenyl)-N-methyl-N-[(3-methyloxetan-3-yl)methyl]methanamine + H2O = 2-({[(4-methoxyphenyl)methyl](methyl)amino}methyl)-2-methylpropane-1,3-diol
(2)
-
-
-
cis-stilbene oxide + H2O = (1R,2R)-1,2-diphenylethane-1,2-diol
cis-stilbene oxide + H2O = (1R,2R)-1,2-diphenylethane-1,2-diol
active site structure, quantitative structure-activity relationships, molecular modelling
-
cis-stilbene oxide + H2O = (1R,2R)-1,2-diphenylethane-1,2-diol
formation of threo-1,2-diphenyl-1,2-ethanediols from all epoxides involving anti-stereospecific opening of the oxirane ring with about 90% preference for the (S)-carbon to give nearly optically pure (R,R)-diols
-
cis-stilbene oxide + H2O = (1R,2R)-1,2-diphenylethane-1,2-diol
reaction mechanism, catalytic triad
-
cis-stilbene oxide + H2O = (1R,2R)-1,2-diphenylethane-1,2-diol
reaction mechanism, catalytic triad
-
cis-stilbene oxide + H2O = (1R,2R)-1,2-diphenylethane-1,2-diol
reaction mechanism, catalytic triad
-
cis-stilbene oxide + H2O = (1R,2R)-1,2-diphenylethane-1,2-diol
reaction mechanism, catalytic triad
-
cis-stilbene oxide + H2O = (1R,2R)-1,2-diphenylethane-1,2-diol
reaction mechanism, catalytic triad
-
cis-stilbene oxide + H2O = (1R,2R)-1,2-diphenylethane-1,2-diol
reaction mechanism, catalytic triad
-
cis-stilbene oxide + H2O = (1R,2R)-1,2-diphenylethane-1,2-diol
reaction mechanism, catalytic triad
-
cis-stilbene oxide + H2O = (1R,2R)-1,2-diphenylethane-1,2-diol
reaction mechanism, catalytic triad
-
cis-stilbene oxide + H2O = (1R,2R)-1,2-diphenylethane-1,2-diol
reaction mechanism, catalytic triad
-
cis-stilbene oxide + H2O = (1R,2R)-1,2-diphenylethane-1,2-diol
the catalytic triad is Asp223-Glu402-His429, the active site includes an oxyanion hole
-
cis-stilbene oxide + H2O = (1R,2R)-1,2-diphenylethane-1,2-diol
the catalytic triad is Asp226-His431-Asp352, catalytic mechanism involving an ester intermediate formed by alkylation of an active site carboxyl group
-
cis-stilbene oxide + H2O = (1R,2R)-1,2-diphenylethane-1,2-diol
two step mechanism with formation of of a hydroxyl-alkyl-enzyme intermediate, catalytic triad
-
cis-stilbene oxide + H2O = (1R,2R)-1,2-diphenylethane-1,2-diol
two step mechanism with formation of of a hydroxyl-alkyl-enzyme intermediate, catalytic triad
-
cis-stilbene oxide + H2O = (1R,2R)-1,2-diphenylethane-1,2-diol
two step mechanism with formation of of a hydroxyl-alkyl-enzyme intermediate, the catalytic triad is Asp226-His431-Glu404 with polarizing residues Tyr299 and Tyr374
-
cis-stilbene oxide + H2O = (1R,2R)-1,2-diphenylethane-1,2-diol
(1)
-
-
-
cis-stilbene oxide + H2O = (1R,2R)-1,2-diphenylethane-1,2-diol
ring-opening reaction mechanism, overview
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(3-(4-(2-oxa-6-azaspiro[3.3]heptan-6-ylmethyl)phenoxy)azetidin-1-yl)(5-(4-ethoxyphenyl)-1,3,4-oxadiazol-2-yl)methanone + H2O
(3-[4-[([[3-(hydroxymethyl)oxetan-3-yl]methyl]amino)methyl]phenoxy]azetidin-1-yl)[5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methanone
-
-
-
-
?
(3-(4-(2-oxa-6-azaspiro[3.3]heptan-6-ylmethyl)phenoxy)azetidin-1-yl)(5-(4-ethoxyphenyl)-1,3,4-oxadiazol-2-yl)methanone + H2O
?
-
-
-
-
?
(3-(4-(2-oxa-6-azaspiro[3.3]heptan-6-ylmethyl)phenoxy)azetidin-1-yl)(5-(4-ethoxyphenyl)-1,3,4-oxadiazol-2-yl)methanone + H2O
[3-(4-[[3,3-bis(hydroxymethyl)azetidin-1-yl]methyl]phenoxy)azetidin-1-yl][5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methanone
-
-
-
-
?
(5Z,11Z,14Z)-8,9-epoxyeicosatrienoic acid + H2O
(5Z,11Z,14Z)-8,9-dihydroxyeicosatrienoic acid
(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,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
(8Z,11Z,14Z)-5,6-epoxyeicosatrienoic acid + H2O
(8Z,11Z,14Z)-5,6-dihydroxyeicosatrienoic acid
(exo)-2,3-epoxynorbornane + H2O
?
-
-
-
-
?
(R)-1,2-epoxybutane + H2O
(2R)-butane-1,2-diol
very limited preference for hydrolysis of the (R)-enantiomer
-
-
?
(R)-1,2-epoxyhexane + H2O
n-2-hydroxyhexanol
-
-
-
-
?
(R)-epichlorhydrin + H2O
(R)-3-chloro-1,2-propanediol
very limited preference for hydrolysis of the (S)-enantiomer
-
-
?
(R)-glycidyl tosylate + H2O
(2R)-4-(4-methylbenzene-1-sulfonyl)butane-1,2,4-triol
very limited preference for hydrolysis of the (R)-enantiomer
-
-
?
(R)-styrene oxide + H2O
(1R)-1-phenylethane-1,2-diol
(R)-styrene oxide + H2O
(R)-styrene glycol
preferential hydrolysis of the (R)-enantiomer
-
-
?
(S)-1,2-epoxybutane + H2O
(2S)-butane-1,2-diol
very limited preference for hydrolysis of the (R)-enantiomer
-
-
?
(S)-1,2-epoxyhexane + H2O
n-2-hydroxyhexanol
-
-
-
-
?
(S)-epichlorhydrin + H2O
(S)-3-chloro-1,2-propanediol
very limited preference for hydrolysis of the (S)-enantiomer
-
-
?
(S)-glycidyl tosylate + H2O
(2S)-4-(4-methylbenzene-1-sulfonyl)butane-1,2,4-triol
very limited preference for hydrolysis of the (R)-enantiomer
-
-
?
(S)-styrene oxide + H2O
1,2-diphenylethane-1,2-diol
-
-
-
-
?
1,10-phenanthroline 5,6-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
?
1,2,3,4,9,9-hexachloro-6,7-epoxy-1,4,4a,5,6,7,8,8a-octahydro-1,4-methanonaphthalene + H2O
1,2,3,4,9,9-hexachloro-1,4,4a,5,6,7,8,8a-octahydro-1,4-methanonaphthalene-6,7-diol
1,2-epoxybutane + H2O
2-hydroxy-n-butanol
-
-
-
-
?
1-(4-methoxyphenyl)-N-methyl-N-[(3-methyloxetan-3-yl)methyl]methanamine + H2O
2-([[(4-methoxyphenyl)methyl](methyl)amino]methyl)-2-methylpropane-1,3-diol
-
-
-
ir
1-methyl-1-phenyloxirane + H2O
?
1-[3-[4-([methyl[(3-methyloxetan-3-yl)methyl]amino]methyl)phenoxy]azetidin-1-yl]ethan-1-one + H2O
1-[3-[4-([[3-hydroxy-2-(hydroxymethyl)-2-methylpropyl](methyl)amino]methyl)phenoxy]azetidin-1-yl]ethan-1-one
-
[3-hydroxy-2-(hydroxymethyl)-2-methylpropyl](methyl)amino]methyl)phenoxy]azetidin-1-yl]ethan-1-one
-
ir
11,12-epoxyeicosatrienoate + H2O
11,12-hydroxyeicosatrienoate
-
-
-
?
14,15-epoxyeicosatrienoic acid + H2O
?
-
-
-
?
16,17-epoxyandrost-4-en-3-one + H2O
16,17-dihydroxyandrost-4-en-3-one
16alpha,17alpha-epoxyandrosten-3-one + H2O
?
2,3-epoxypropyl ether + H2O
?
-
-
-
-
?
2,3-epoxypropyl-p-methoxyphenyl ether + H2O
3-(3-methoxyphenoxy)propane-1,2-diol
-
-
-
-
?
2,3-epoxypropyl-p-methoxyphenyl ether + H2O
?
-
-
-
-
?
2-(4-methoxyphenyl)-N-methyl-N-[(3-methyloxetan-3-yl)methyl]ethan-1-amine + H2O
2-([[2-(4-methoxyphenyl)ethyl](methyl)amino]methyl)-2-methylpropane-1,3-diol
-
-
-
ir
2-arachidonoylglycerol + H2O
arachidonic acid + glycerol
-
-
-
-
?
2-bromoethylene oxide + H2O
?
-
-
-
-
?
2-chloroethylene oxide + H2O
?
2-methyl styrene oxide + H2O
(2R)-2-phenylpropane-1,2-diol
-
-
highly enantioselective in ionic liquid [bmim][PF6]in presence of 10% water
-
?
3,3,3-trichloropropylene oxide + H2O
?
-
-
-
-
?
3-methylcholanthrene 11,12-oxide + H2O
?
4-chlorophenyl 2,3-epoxypropyl ether + H2O
?
4-methyl-2-oxo-2H-chromen-7-yl oxiran-2-ylmethyl carbonate + H2O
?
4-nitrophenyl 3-(oxiran-2-yl)propanoate + H2O
?
4-nitrophenyl 6-oxabicyclo[3.1.0]hexane-3-carboxylate + H2O
?
4-nitrostyrene 7,8-oxide + H2O
1-(4-nitro)phenyl-ethane-1,2-diol
-
i.e. PNSO
-
-
?
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
-
?
4-vinylcyclohexene + H2O
?
4-vinylcyclohexene diepoxide + H2O
4-(1,2-dihydroxy)ethyl-1,2-dihydroxycyclohexane
4-vinylcyclohexene dioxide + H2O
?
-
low activity
-
-
?
7,12-dimethylbenz[a]anthracene + 3 H2O
7,12-dimethylbenz[a]anthra-3,4-diol-1,2-epoxide
-
-
-
?
7,12-dimethylbenz[a]anthracene + 3 H2O
7,12-dimethylbenz[a]anthracene-3,4-diol-1,2-epoxide
7,12-dimethylbenz[a]anthracene + H2O
?
-
-
-
-
?
7-glycidoxycoumarin + H2O
7-(1',2'-dihydroxy-3'-propoxy)coumarin
-
substrate is a stable epoxide
-
-
?
7-glycidoxycoumarin + H2O
?
-
-
-
-
?
7-methylbenzanthracene-5,6-oxide + H2O
?
-
-
-
-
?
7-methylbenzoanthracene + H2O
?
-
-
-
-
?
aflatoxin-B1-8,9-exo-epoxide + H2O
?
allylbenzene + H2O
3-phenylpropane-1,2-diol
androstene oxide + H2O
androstene diol
-
-
-
?
benzene oxide + H2O
?
-
-
-
-
?
benzo(a)pyrene 4,5-oxide + H2O
?
-
-
-
-
?
benzoanthracene 5,6-oxide + H2O
?
benzoanthracene-9,10-oxide + H2O
?
-
-
-
-
?
benzopyrene 11,12-oxide + H2O
?
-
-
-
-
?
benzopyrene 4,5-oxide + H2O
(-)benzopyrene 4,5-dihydrodiol
benzopyrene 7,8-oxide + H2O
?
benzopyrene 9,10-oxide + H2O
?
-
-
-
-
?
benzo[a]pyrene 5-oxide + H2O
?
benzo[a]pyrene 7,8-oxide + H2O
benzo[a]pyrene 7,8-diol
-
-
-
?
benzo[a]pyrene-7,8-epoxide + H2O
benzo[a]pyrene-7,8-dihydrodiol
benz[a]anthracene 5,6-oxide + H2O
5,6-dihydro-chrysene-5,6-diol
-
-
-
-
?
benz[a]pyrene 4,5-oxide + H2O
4,5-dihydro-benzo[def]chrysene-4,5-diol
-
-
-
-
?
bisnorsqualene oxide + H2O
?
-
-
-
-
?
butadiene + H2O
butadienol
-
-
-
?
butadiene monoxide + H2O
?
-
low activity
-
-
?
carbamazepine-10,11-epoxide + H2O
?
cis-(9R,10S)-epoxystearic acid + H2O
threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid
cis-(9R,10S)-epoxystearic acid methyl ester + H2O
threo-(9R,10R)-dihydroxystearic acid methyl ester + threo-(9S,10S)-dihydroxystearic acid methyl ester
cis-(9S,10R)-epoxystearic acid + H2O
threo-(9R,10R)-dihydroxystearic acid + threo-(9S,10S)-dihydroxystearic acid
cis-(9S,10R)-epoxystearic acid methyl ester + H2O
threo-(9R,10R)-dihydroxystearic acid methyl ester + threo-(9S,10S)-dihydroxystearic acid methyl ester
cis-4,4'-dichlorostilbene oxide + H2O
(1R,2R)-1,2-bis(4-chlorophenyl)ethane-1,2-diol
-
-
product identification
-
?
cis-4,4'-diethylstilbene oxide + H2O
(1R,2R)-1,2-bis(4-ethylphenyl)ethane-1,2-diol
-
-
product identification
-
?
cis-4,4'-diisopropylstilbene oxide + H2O
(1R,2R)-1,2-bis(4-isopropylphenyl)ethane-1,2-diol
-
-
product identification
-
?
cis-4,4'-dimethylstilbene oxide + H2O
(1R,2R)-1,2-bis(4-methylphenyl)ethane-1,2-diol
-
-
product identification
-
?
cis-8-ethylstyrene 7,8-oxide + H2O
?
-
-
-
-
?
cis-stilbene oxide + H2O
(+)-(1R,2R)-1,2-diphenylethane-1,2-diol
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
?
cyano(2-methoxynaphthalen-6-yl)methyl trans-(2-(3-phenyloxiran-2-yl))acetate + H2O
?
-
-
-
?
cyano(2-methoxynaphthalen-6-yl)methyl trans-2-(3-propyloxiran-2-yl)acetate + H2O
?
cyano(6-methoxy-naphthalen-2-yl)methyl glycidyl carbonate + H2O
?
cyano(6-methoxy-naphthalen-2-yl)methyl oxiran-2-ylmethyl carbonate + H2O
?
-
-
-
?
cyano(6-methoxy-naphthalen-2-yl)methyl trans-[(3-phenyloxiran-2-yl)methyl]carbonate + H2O
?
-
-
-
?
cyano-(6-methoxy-naphthalen-2-yl)-methyl 3,3-dimethyl-oxiranylmethyl carbonate + H2O
?
-
-
-
?
cyano-(6-methoxy-naphthalen-2-yl)-methyl trans-((3-ethyl-oxiran-2-yl)methyl) carbonate + H2O
?
-
-
-
?
cyano-(6-methoxynaphthalen-2-yl)methyl trans-2-pentenylacetate + H2O
?
-
prepared from trans-styrylacetic acid and 7-methoxy-2-naphthaldehyde. Enzyme EH catalyzed hydrolysis of the epoxide substrate produces an intermediate diol which lactonizes to release a fluorescent reporter after hydrolysis of the intermediate cyanohydrin
-
-
?
cyclododecene-1,2-oxide + H2O
?
-
-
-
-
?
cyclohexene + H2O
cyclohexadiol
-
-
-
?
cyclohexene oxide + H2O
?
-
-
-
-
?
cyclohexene-1,2-oxide + H2O
?
-
-
-
-
?
cytochrome P450 isoform 1B1 + H2O
7,12-dimethylbenz(a)anthracene-3,4-diol
di(2-ethylhexyl)phthalate + H2O
?
dibenzanthracene 5,6-oxide + H2O
?
dibenzoanthracene + H2O
?
-
-
-
-
?
dihydronaphthalene oxide + H2O
(1S,2S)-1,2,3,4-tetrahydronaphthalene-1,2-diol
-
-
highly enantioselective in ionic liquid [bmim][PF6]in presence of 10% water
-
?
dl-1,3-butadiene diepoxide + H2O
?
-
low activity
-
-
?
epibromhydrin + H2O
?
-
-
-
-
?
epichlorhydrin + H2O
3-chloro-1,2-propanediol
-
-
-
-
?
epifluorohydrin + H2O
?
-
-
-
-
?
epoxy-stearic acid + H2O
?
-
highly enantiospecific reaction, low activity
-
-
?
epoxyestratrienol + H2O
?
-
-
-
?
epoxyestratrienol + H2O
dihydroxyestratrienol
-
-
-
?
ethylene oxide + H2O
ethane-1,2-diol
ethylene oxide + H2O
ethylene glycol
-
-
-
?
glycidyl methacrylate + H2O
?
-
low activity
-
-
?
indene-1,2-oxide + H2O
?
-
-
-
-
?
juvenile hormone I + H2O
?
-
-
-
-
?
juvenile hormone II + H2O
?
-
-
-
-
?
juvenile hormone III + H2O
?
naphthalene 1,2-oxide + H2O
naphthalene 1,2-diol
-
-
-
-
?
naphthalene-1,2-oxide + H2O
?
octene 1,2-oxide + H2O
octan-1,2-diol
-
-
-
-
?
octene-1,2-oxide + H2O
?
-
-
-
-
?
okadaic acid + H2O
?
-
-
-
-
?
p-chlorophenyl-2,3-epoxypropylether + H2O
?
-
-
-
-
?
p-nitrostyrene 7,8-oxide + H2O
?
phenanthrene-9,10-oxide + H2O
?
3.3.2.9 microsomal epoxide hydrolase
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