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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

Reaction

1,2-epoxymenth-8-ene
+
H2O
=
menth-8-ene-1,2-diol

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

     3 Hydrolases
         3.3 Acting on ether bonds
             3.3.2 Ether hydrolases
                3.3.2.8 limonene-1,2-epoxide hydrolase

Substrates Products

Substrates Products on EC 3.3.2.8 - limonene-1,2-epoxide hydrolase

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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
(-)-limonene oxide + H2O
(1R,2R,4S)-limonene-1,2-diol
show the reaction diagram
-
-
-
?
(1R,2S)-1-methylcyclohexane oxide + H2O
(1S,2S)-1-methylcyclohexane-1,2-diol
show the reaction diagram
-
-
-
ir
(1R,2S,4R)-limonene-1,2-epoxide + H2O
(1R,2S,4R)-limonene-1,2-diol
show the reaction diagram
(1R,2S,4R)-limonene-1,2-epoxide + H2O
(1S,2S,4R)-limonene-1,2-diol
show the reaction diagram
(1R,2S,4S)-limonene-1,2-epoxide + H2O
(1R,2R,4S)-limonene-1,2-diol
show the reaction diagram
(1S,2R)-1-methylcyclohexane oxide + H2O
(1R,2R)-1-methylcyclohexane-1,2-diol
show the reaction diagram
-
-
-
ir
(1S,2R,4R)-limonene-1,2-epoxide + H2O
(1S,2R,4R)-limonene-1,2-diol
show the reaction diagram
(1S,2R,4R)-limonene-1,2-epoxide + H2O
(1S,2S,4R)-limonene-1,2-diol
show the reaction diagram
(1S,2R,4S)-limonene-1,2-epoxide + H2O
(1R,2R,4S)-limonene-1,2-diol
show the reaction diagram
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
show the reaction diagram
-
-
optically pure, diastereomeric excess above 99%
?
(4R)-limonene-1,2-epoxide + H2O
(4R)-limonene-1,2-diol
show the reaction diagram
(4R)-limonene-1,2-epoxide + H2O
?
show the reaction diagram
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
(4S)-limonene-1,2-diol
show the reaction diagram
(4S)-limonene-1,2-epoxide + H2O
?
show the reaction diagram
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
show the reaction diagram
-
-
-
?
1,2-epoxy-2-methyl-6-heptene + H2O
(2S)-2-methyl-6-heptene-1,2-diol
show the reaction diagram
-
-
-
?
1,2-epoxy-2-methylheptane + H2O
(2S)-2-methylheptane-1,2-diol
show the reaction diagram
-
-
-
?
1,2-epoxy-3-benzyl-2-methylpropane + H2O
(2S)-3-benzyl-2-methylpropane-1,2-diol
show the reaction diagram
-
-
-
?
1-methylcyclohexene oxide + H2O
(1S,2S)-1-methylcyclohexane-1,2-diol
show the reaction diagram
-
-
-
?
1-methylcyclohexene oxide + H2O
1-methylcyclohexane-1,2-diol
show the reaction diagram
2 cyclohexene-1,2-epoxide + 2 H2O
(S,S)-cyclohexane-1,2-diol + (R,R)-cyclohexane-1,2-diol
show the reaction diagram
2-butyloxirane + H2O
hexane-1,2-diol
show the reaction diagram
4-(1-methylethenyl)-cyclohexan-1,2-epoxide + H2O
4-(1-methylethenyl)-cyclohexan-1,2-diol
show the reaction diagram
-
-
-
?
cycloheptene-1,2-epoxide + H2O
cycloheptene-1,2-diol
show the reaction diagram
cyclohexene oxide + H2O
(1S,2S)-trans cyclohexanediol + (1R,2R)-trans-cyclohexanediol
show the reaction diagram
-
-
-
?
cyclohexene oxide + H2O
cyclohexane-1,2-diol
show the reaction diagram
cyclohexene-1,2-epoxide + H2O
(R1,R2)-cyclohexane-1,2-diol
show the reaction diagram
-
-
-
-
?
cyclohexene-1,2-epoxide + H2O
(S1,S2)-cyclohexane-1,2-diol
show the reaction diagram
-
-
-
-
?
cyclohexene-1,2-epoxide + H2O
cyclohexane-1,2-diol
show the reaction diagram
cyclopentene-1,2-epoxide + H2O
(R1,R2)-cyclopentane-1,2-diol
show the reaction diagram
-
-
-
-
?
cyclopentene-1,2-epoxide + H2O
(S1,S2)-cyclopentane-1,2-diol
show the reaction diagram
-
-
-
-
?
cyclopentene-1,2-epoxide + H2O
cyclopentane-1,2-diol
show the reaction diagram
cyclopentene-oxide + H2O
(R,R)-cyclopentene-1,2-diol + (S,S)-cyclopentene-1,2-diol
show the reaction diagram
indene oxide + H2O
indane-1,2-diol
show the reaction diagram
limonene-1,2-epoxide + H2O
(1R,2R,4S)-limonene-1,2-diol
show the reaction diagram
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
show the reaction diagram
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
-
-
?
limonene-1,2-epoxide + H2O
(1S,2S,4R)-limonene-1,2-diol + (1R,2R,4S)-limonene-1,2-diol
show the reaction diagram
limonene-1,2-epoxide + H2O
limonene-1,2-diol
show the reaction diagram
phenylethylenoxide + H2O
1-phenylethane-1,2-diol
show the reaction diagram
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
show the reaction diagram
rac-2-(phenoxymethyl)oxirane + H2O
(2S)-2-(phenoxymethyl)oxirane + (2R)-3-phenoxypropane-1,2-diol
show the reaction diagram
S-(-)-limonene + H2O
limonene-1,2-diol
show the reaction diagram
styrene-7,8-oxide + H2O
styrene-7,8-diol
show the reaction diagram
-
-
-
?
additional information
?
-