Any feedback?
Please rate this page
(literature.php)
(0/150)

BRENDA support

Literature summary for 3.3.2.8 extracted from

  • Hopmann, K.H.; Hallberg, B.M.; Himo, F.
    Catalytic mechanism of limonene epoxide hydrolase, a theoretical study (2005), J. Am. Chem. Soc., 127, 14339-14347.
    View publication on PubMed
Search for more literature for 3.3.2.8

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
limonene-1,2-epoxide + H2O Rhodococcus erythropolis part of limonene degradation pathway which allows the organism to grow on limone as sole source of carbon and energy limonene-1,2-diol
-
 ir
limonene-1,2-epoxide + H2O Rhodococcus erythropolis DCL14 part of limonene degradation pathway which allows the organism to grow on limone as sole source of carbon and energy limonene-1,2-diol
-
 ir

Organism

Organism UniProt Comment Textmining
Rhodococcus erythropolis Q9ZAG3 DCL14
-
Rhodococcus erythropolis DCL14 Q9ZAG3 DCL14
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(1R,2S)-1-methylcyclohexane oxide + H2O
-
 Rhodococcus erythropolis (1S,2S)-1-methylcyclohexane-1,2-diol
-
 ir
(1R,2S,4R)-limonene-1,2-epoxide + H2O 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 Rhodococcus erythropolis (1S,2S,4R)-limonene-1,2-diol
-
 ir
(1R,2S,4R)-limonene-1,2-epoxide + H2O 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 Rhodococcus erythropolis DCL14 (1S,2S,4R)-limonene-1,2-diol
-
 ir
(1R,2S,4S)-limonene-1,2-epoxide + H2O 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 Rhodococcus erythropolis (1R,2R,4S)-limonene-1,2-diol
-
 ir
(1R,2S,4S)-limonene-1,2-epoxide + H2O 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 Rhodococcus erythropolis DCL14 (1R,2R,4S)-limonene-1,2-diol
-
 ir
(1S,2R)-1-methylcyclohexane oxide + H2O
-
 Rhodococcus erythropolis (1R,2R)-1-methylcyclohexane-1,2-diol
-
 ir
(1S,2R,4R)-limonene-1,2-epoxide + H2O 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 Rhodococcus erythropolis (1S,2S,4R)-limonene-1,2-diol
-
 ir
(1S,2R,4R)-limonene-1,2-epoxide + H2O 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 Rhodococcus erythropolis DCL14 (1S,2S,4R)-limonene-1,2-diol
-
 ir
(1S,2R,4S)-limonene-1,2-epoxide + H2O 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 Rhodococcus erythropolis (1R,2R,4S)-limonene-1,2-diol
-
 ir
limonene-1,2-epoxide + H2O
-
 Rhodococcus erythropolis limonene-1,2-diol
-
 ir
limonene-1,2-epoxide + H2O part of limonene degradation pathway which allows the organism to grow on limone as sole source of carbon and energy Rhodococcus erythropolis limonene-1,2-diol
-
 ir
limonene-1,2-epoxide + H2O
-
 Rhodococcus erythropolis DCL14 limonene-1,2-diol
-
 ir
limonene-1,2-epoxide + H2O part of limonene degradation pathway which allows the organism to grow on limone as sole source of carbon and energy Rhodococcus erythropolis DCL14 limonene-1,2-diol
-
 ir