3.3.2.8: limonene-1,2-epoxide hydrolase
This is an abbreviated version!
For detailed information about limonene-1,2-epoxide hydrolase, go to the full flat file.
Word Map on EC 3.3.2.8
-
3.3.2.8
-
stereoselective
-
rhodococcus
-
erythropolis
-
hydrolases
-
desymmetrization
-
cyclohexene
-
enantioselective
-
alphabet
-
regioselective
-
lining
-
six-stranded
-
astronomically
-
intricacies
-
valpromide
-
selenomethionine-substituted
-
biocatalysis
-
single-wavelength
-
wide-ranging
-
diols
-
polyketide
-
cyclopentene
-
synthesis
- 3.3.2.8
-
stereoselective
- rhodococcus
- erythropolis
- hydrolases
-
desymmetrization
- cyclohexene
-
enantioselective
-
alphabet
-
regioselective
-
lining
-
six-stranded
-
astronomically
-
intricacies
- valpromide
-
selenomethionine-substituted
-
biocatalysis
-
single-wavelength
-
wide-ranging
- diols
- polyketide
-
cyclopentene
- synthesis
Reaction
Synonyms
CH55-LEH, LEH, limA, limonene 1,2-epoxide hydrolase, limonene epoxide hydrolase, limonene oxide hydrolase, limonene-1,2-epoxide hydrolase, Re-LEH, Tomsk-LEH
ECTree
Advanced search results
Substrates Products
Substrates Products on EC 3.3.2.8 - limonene-1,2-epoxide hydrolase
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
REACTION DIAGRAM
(-)-limonene oxide + H2O
(1R,2R,4S)-limonene-1,2-diol
-
-
-
?
(1R,2S)-1-methylcyclohexane oxide + H2O
(1S,2S)-1-methylcyclohexane-1,2-diol
-
-
-
ir
(1S,2R)-1-methylcyclohexane oxide + H2O
(1R,2R)-1-methylcyclohexane-1,2-diol
-
-
-
ir
(1S,2R,4S)-limonene-1,2-epoxide + H2O
(1R,2R,4S)-limonene-1,2-diol
the reaction mechanism involves epoxide protonation by Asp109, nucleophilic attack by water, and abstraction of a proton from water by Asp132. The isopropenyl group plays a crucial role because it restricts the half-chair conformation to one of the two possible helicities. In this conformation, attack on the different epoxide carbons will lead to either a chair-like or a twist-boat transition state structure, the latter resulting in a higher barrier. The regioselectivity is thus governed by conformational and not electronic factors
-
-
ir
(1S2R4S)-limonene-1,2-epoxide + H2O
(1R,2R,4S)-limonene-1,2-diol
-
-
optically pure, diastereomeric excess above 99%
?
(4R)-limonene-1,2-epoxide + H2O
?
the mixture of cis (1R,2S,4R) and trans (1S,2R,4R) isomers of (+)-limonene-1,2-epoxide and the mixture of cis (1S,2R,4S) and trans (1R,2S,4S) isomers of (-)-limonene-1,2-epoxide are quantitatively converted into the diaxial (1S,2S,4R)- and (1R,2R,4S)-limonene-1,2-diols, respectively. Cyclopentene-1,2-epoxide is no substrate for enzyme CH55-LEH. Enzyme substrate specificity and stereospecificity, overview
-
-
?
(4S)-limonene-1,2-epoxide + H2O
?
the mixture of cis (1R,2S,4R) and trans (1S,2R,4R) isomers of (+)-limonene-1,2-epoxide and the mixture of cis (1S,2R,4S) and trans (1R,2S,4S) isomers of (-)-limonene-1,2-epoxide are quantitatively converted into the diaxial (1S,2S,4R)- and (1R,2R,4S)-limonene-1,2-diols, respectively. Cyclopentene-1,2-epoxide is no substrate for enzyme CH55-LEH. Enzyme substrate specificity and stereospecificity, overview
-
-
?
1,2-epoxy-2,6-dimethyl-5-heptene + H2O
(2S)-2,6-dimethyl-5-hepten-1,2-diol
-
-
-
?
1,2-epoxy-2-methyl-6-heptene + H2O
(2S)-2-methyl-6-heptene-1,2-diol
-
-
-
?
1,2-epoxy-2-methylheptane + H2O
(2S)-2-methylheptane-1,2-diol
-
-
-
?
1,2-epoxy-3-benzyl-2-methylpropane + H2O
(2S)-3-benzyl-2-methylpropane-1,2-diol
-
-
-
?
1-methylcyclohexene oxide + H2O
(1S,2S)-1-methylcyclohexane-1,2-diol
-
-
-
?
4-(1-methylethenyl)-cyclohexan-1,2-epoxide + H2O
4-(1-methylethenyl)-cyclohexan-1,2-diol
-
-
-
?
cyclohexene oxide + H2O
(1S,2S)-trans cyclohexanediol + (1R,2R)-trans-cyclohexanediol
-
-
-
?
limonene-1,2-epoxide + H2O
(1R,2R,4S)-limonene-1,2-diol
enantiomeric mixtures of (+)-limone oxide, overview. Enzyme CH55-LEH prefers the cis form of (-)-limonene oxide
-
-
?
limonene-1,2-epoxide + H2O
(1S,2S,4R)-limonene-1,2-diol
enantiomeric mixtures of (+)-limone oxide, overview. Enzyme Tomsk-LEH shows stereospecificity in the hydrolysis of cis/trans mixtures of (+)-limonene oxide by preferring the trans isomer
-
-
?
rac-1-methyl-7-oxabicyclo[4.1.0]heptane + H2O
(1S,2S)-1-methylcyclohexane-1,2-diol + (1R,6S)-1-methyl-7-oxabicyclo[4.1.0]heptane
rac-2-(phenoxymethyl)oxirane + H2O
(2S)-2-(phenoxymethyl)oxirane + (2R)-3-phenoxypropane-1,2-diol
(1R,2S,4R)-limonene-1,2-diol
-
-
-
?
(1R,2S,4R)-limonene-1,2-epoxide + H2O
(1R,2S,4R)-limonene-1,2-diol
-
-
-
?
(1S,2S,4R)-limonene-1,2-diol
-
-
optically pure, diastereomeric excess above 99%
?
(1R,2S,4R)-limonene-1,2-epoxide + H2O
(1S,2S,4R)-limonene-1,2-diol
the reaction mechanism involves epoxide protonation by Asp109, nucleophilic attack by water, and abstraction of a proton from water by Asp132. The isopropenyl group plays a crucial role because it restricts the half-chair conformation to one of the two possible helicities. In this conformation, attack on the different epoxide carbons will lead to either a chair-like or a twist-boat transition state structure, the latter resulting in a higher barrier. The regioselectivity is thus governed by conformational and not electronic factors
-
-
ir
(1R,2S,4R)-limonene-1,2-epoxide + H2O
(1S,2S,4R)-limonene-1,2-diol
the reaction mechanism involves epoxide protonation by Asp109, nucleophilic attack by water, and abstraction of a proton from water by Asp132. The isopropenyl group plays a crucial role because it restricts the half-chair conformation to one of the two possible helicities. In this conformation, attack on the different epoxide carbons will lead to either a chair-like or a twist-boat transition state structure, the latter resulting in a higher barrier. The regioselectivity is thus governed by conformational and not electronic factors
-
-
ir
(1R,2R,4S)-limonene-1,2-diol
-
-
optically pure, diastereomeric excess above 99%
?
(1R,2S,4S)-limonene-1,2-epoxide + H2O
(1R,2R,4S)-limonene-1,2-diol
the reaction mechanism involves epoxide protonation by Asp109, nucleophilic attack by water, and abstraction of a proton from water by Asp132. The isopropenyl group plays a crucial role because it restricts the half-chair conformation to one of the two possible helicities. In this conformation, attack on the different epoxide carbons will lead to either a chair-like or a twist-boat transition state structure, the latter resulting in a higher barrier. The regioselectivity is thus governed by conformational and not electronic factors
-
-
ir
(1R,2S,4S)-limonene-1,2-epoxide + H2O
(1R,2R,4S)-limonene-1,2-diol
the reaction mechanism involves epoxide protonation by Asp109, nucleophilic attack by water, and abstraction of a proton from water by Asp132. The isopropenyl group plays a crucial role because it restricts the half-chair conformation to one of the two possible helicities. In this conformation, attack on the different epoxide carbons will lead to either a chair-like or a twist-boat transition state structure, the latter resulting in a higher barrier. The regioselectivity is thus governed by conformational and not electronic factors
-
-
ir
(1S,2R,4R)-limonene-1,2-diol
-
-
-
?
(1S,2R,4R)-limonene-1,2-epoxide + H2O
(1S,2R,4R)-limonene-1,2-diol
-
-
-
?
(1S,2S,4R)-limonene-1,2-diol
-
-
optically pure, diastereomeric excess above 99%
?
(1S,2R,4R)-limonene-1,2-epoxide + H2O
(1S,2S,4R)-limonene-1,2-diol
the reaction mechanism involves epoxide protonation by Asp109, nucleophilic attack by water, and abstraction of a proton from water by Asp132. The isopropenyl group plays a crucial role because it restricts the half-chair conformation to one of the two possible helicities. In this conformation, attack on the different epoxide carbons will lead to either a chair-like or a twist-boat transition state structure, the latter resulting in a higher barrier. The regioselectivity is thus governed by conformational and not electronic factors
-
-
ir
(1S,2R,4R)-limonene-1,2-epoxide + H2O
(1S,2S,4R)-limonene-1,2-diol
the reaction mechanism involves epoxide protonation by Asp109, nucleophilic attack by water, and abstraction of a proton from water by Asp132. The isopropenyl group plays a crucial role because it restricts the half-chair conformation to one of the two possible helicities. In this conformation, attack on the different epoxide carbons will lead to either a chair-like or a twist-boat transition state structure, the latter resulting in a higher barrier. The regioselectivity is thus governed by conformational and not electronic factors
-
-
ir
(4R)-limonene-1,2-diol
-
-
-
?
(4R)-limonene-1,2-epoxide + H2O
(4R)-limonene-1,2-diol
-
-
-
?
(4S)-limonene-1,2-diol
-
-
-
?
(4S)-limonene-1,2-epoxide + H2O
(4S)-limonene-1,2-diol
-
-
-
?
1-methylcyclohexane-1,2-diol
-
-
-
?
1-methylcyclohexene oxide + H2O
1-methylcyclohexane-1,2-diol
-
-
-
?
(S,S)-cyclohexane-1,2-diol + (R,R)-cyclohexane-1,2-diol
LEH is the catalyst in the hydrolytic desymmetrization of cyclohexene oxide with formation of (R,R)- and (S,S)-cyclohexene-1,2-diol. Wild-type LEH shows an enanioselectivity of 2% enantiomeric excess (S,S), analysis of (R,R)- and (S,S)-selective LEH mutant variants (80-94% enantiomeric excess)
-
-
?
2 cyclohexene-1,2-epoxide + 2 H2O
(S,S)-cyclohexane-1,2-diol + (R,R)-cyclohexane-1,2-diol
LEH is the catalyst in the hydrolytic desymmetrization of cyclohexene oxide with formation of (R,R)- and (S,S)-cyclohexene-1,2-diol. Wild-type LEH shows an enanioselectivity of 2% enantiomeric excess (S,S), analysis of (R,R)- and (S,S)-selective LEH mutant variants (80-94% enantiomeric excess)
-
-
?
cycloheptene-1,2-epoxide + H2O
cycloheptene-1,2-diol
-
-
-
?
cyclohexene-1,2-epoxide + H2O
cyclohexane-1,2-diol
0.25% activity compared to limonene-1,2-epoxide
-
-
?
cyclohexene-1,2-epoxide + H2O
cyclohexane-1,2-diol
0.25% activity compared to limonene-1,2-epoxide
-
-
?
cyclohexene-1,2-epoxide + H2O
cyclohexane-1,2-diol
-
-
-
?
cyclopentane-1,2-diol
low activity
-
-
?
cyclopentene-1,2-epoxide + H2O
cyclopentane-1,2-diol
low activity
-
-
?
(R,R)-cyclopentene-1,2-diol + (S,S)-cyclopentene-1,2-diol
-
-
wild-type, 72% conversion, (R,R)-product with 14% enantiomeric excess
-
?
cyclopentene-oxide + H2O
(R,R)-cyclopentene-1,2-diol + (S,S)-cyclopentene-1,2-diol
-
-
wild-type, 72% conversion, (R,R)-product with 14% enantiomeric excess
-
?
(1S,2S,4R)-limonene-1,2-diol + (1R,2R,4S)-limonene-1,2-diol
enantiomeric mixtures of (+)-limone oxide, overview. Re-LEH catalyzes the quantitative conversion of the (+)- and (-)-limonene oxide cis/trans mixtures into the respective diols, the (+)-enantiomer is the better substrate
-
-
?
limonene-1,2-epoxide + H2O
(1S,2S,4R)-limonene-1,2-diol + (1R,2R,4S)-limonene-1,2-diol
enantiomeric mixtures of (+)-limone oxide, overview. Re-LEH catalyzes the quantitative conversion of the (+)- and (-)-limonene oxide cis/trans mixtures into the respective diols, the (+)-enantiomer is the better substrate
-
-
?
limonene-1,2-diol
-
-
-
?
limonene-1,2-epoxide + H2O
limonene-1,2-diol
part of limonene degradation pathway which allows the organism to grow on limone as sole source of carbon and energy
-
-
ir
limonene-1,2-epoxide + H2O
limonene-1,2-diol
limonene-1,2-epoxide is not the natural substrate of Tomsk-LEH
-
-
?
limonene-1,2-epoxide + H2O
limonene-1,2-diol
-
-
-
?
limonene-1,2-epoxide + H2O
limonene-1,2-diol
part of limonene degradation pathway which allows the organism to grow on limone as sole source of carbon and energy
-
-
ir
limonene-1,2-epoxide + H2O
limonene-1,2-diol
-
-
-
?
limonene-1,2-epoxide + H2O
limonene-1,2-diol
-
-
-
?
limonene-1,2-epoxide + H2O
limonene-1,2-diol
limonene-1,2-epoxide is not the natural substrate of CH55-LEH
-
-
?
limonene-1,2-epoxide + H2O
limonene-1,2-diol
limonene-1,2-epoxide is not the natural substrate of Tomsk-LEH
-
-
?
phenylethylenoxide + H2O
1-phenylethane-1,2-diol
-
-
-
?
(1S,2S)-1-methylcyclohexane-1,2-diol + (1R,6S)-1-methyl-7-oxabicyclo[4.1.0]heptane
-
-
wild-type, 99% conversion, 19% enantiomeric excess for (1S,2S)-product
-
?
rac-1-methyl-7-oxabicyclo[4.1.0]heptane + H2O
(1S,2S)-1-methylcyclohexane-1,2-diol + (1R,6S)-1-methyl-7-oxabicyclo[4.1.0]heptane
-
-
wild-type, 99% conversion, 19% enantiomeric excess for (1S,2S)-product
-
?
(2S)-2-(phenoxymethyl)oxirane + (2R)-3-phenoxypropane-1,2-diol
-
-
wild-type, 33% conversion, 37% enantiomeric excess
-
?
rac-2-(phenoxymethyl)oxirane + H2O
(2S)-2-(phenoxymethyl)oxirane + (2R)-3-phenoxypropane-1,2-diol
-
-
wild-type, 33% conversion, 37% enantiomeric excess
-
?
?
-
commercially available cis/trans mixtures of (+)-limonene oxide (59:41 mixture of (1R,2S,4R) and (1S,2R,4R)) and (-)-limonene oxide (55:45 mixture of (1S,2R,4S) and (1R,2S,4S)) are dissolved in CH3CN and diluted with the appropriate LEH-containing buffer solution
-
-
?
additional information
?
-
enantioselectivity and activity of limonene epoxide hydrolase, overview
-
-
?
additional information
?
-
enzyme substrate specificity and stereospecificity, overview
-
-
?
additional information
?
-
-
enzyme substrate specificity and stereospecificity, overview
-
-
?
additional information
?
-
proposed hydrolysis mechanism, the Asp101-Arg99-Asp132 triad with a water molecule is regarded as the active central, overview
-
-
?
additional information
?
-
enantioselectivity and activity of limonene epoxide hydrolase, overview
-
-
?
additional information
?
-
proposed hydrolysis mechanism, the Asp101-Arg99-Asp132 triad with a water molecule is regarded as the active central, overview
-
-
?
additional information
?
-
commercially available cis/trans mixtures of (+)-limonene oxide (59:41 mixture of (1R,2S,4R) and (1S,2R,4R)) and (-)-limonene oxide (55:45 mixture of (1S,2R,4S) and (1R,2S,4S)) are dissolved in CH3CN and diluted with the appropriate LEH-containing buffer solution
-
-
?
additional information
?
-
commercially available cis/trans mixtures of (+)-limonene oxide (59:41 mixture of (1R,2S,4R) and (1S,2R,4R)) and (-)-limonene oxide (55:45 mixture of (1S,2R,4S) and (1R,2S,4S)) are dissolved in CH3CN and diluted with the appropriate LEH-containing buffer solution
-
-
?
additional information
?
-
commercially available cis/trans mixtures of (+)-limonene oxide (59:41 mixture of (1R,2S,4R) and (1S,2R,4R)) and (-)-limonene oxide (55:45 mixture of (1S,2R,4S) and (1R,2S,4S)) are dissolved in CH3CN and diluted with the appropriate LEH-containing buffer solution
-
-
?
additional information
?
-
-
stereochemistry and catalytic mechanism, overview
-
-
?
additional information
?
-
the mixture of cis (1R,2S,4R) and trans (1S,2R,4R) isomers of (+)-limonene-1,2-epoxide and the mixture of cis (1S,2R,4S) and trans (1R,2S,4S) isomers of (-)-limonene-1,2-epoxide are quantitatively converted into the diaxial (1S,2S,4R)- and (1R,2R,4S)-limonene-1,2-diols, respectively. Enzyme substrate specificity and stereospecificity, overview
-
-
?
additional information
?
-
the mixture of cis (1R,2S,4R) and trans (1S,2R,4R) isomers of (+)-limonene-1,2-epoxide and the mixture of cis (1S,2R,4S) and trans (1R,2S,4S) isomers of (-)-limonene-1,2-epoxide are quantitatively converted into the diaxial (1S,2S,4R)- and (1R,2R,4S)-limonene-1,2-diols, respectively. Enzyme substrate specificity and stereospecificity, overview
-
-
?