EC Number |
Substrates |
Organism |
Products |
Reversibility |
---|
3.3.2.8 | (-)-limonene oxide + H2O |
- |
uncultured organism |
(1R,2R,4S)-limonene-1,2-diol |
- |
? |
3.3.2.8 | (1R,2S)-1-methylcyclohexane oxide + H2O |
- |
Rhodococcus erythropolis |
(1S,2S)-1-methylcyclohexane-1,2-diol |
- |
ir |
3.3.2.8 | (1R,2S,4R)-limonene-1,2-epoxide + H2O |
- |
Rhodococcus erythropolis |
(1S,2S,4R)-limonene-1,2-diol |
optically pure, diastereomeric excess above 99% |
? |
3.3.2.8 | (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 |
3.3.2.8 | (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 |
3.3.2.8 | (1R,2S,4R)-limonene-1,2-epoxide + H2O |
- |
Rhodococcus erythropolis |
(1R,2S,4R)-limonene-1,2-diol |
- |
? |
3.3.2.8 | (1R,2S,4R)-limonene-1,2-epoxide + H2O |
- |
uncultured organism |
(1R,2S,4R)-limonene-1,2-diol |
- |
? |
3.3.2.8 | (1R,2S,4S)-limonene-1,2-epoxide + H2O |
- |
Rhodococcus erythropolis |
(1R,2R,4S)-limonene-1,2-diol |
optically pure, diastereomeric excess above 99% |
? |
3.3.2.8 | (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 |
3.3.2.8 | (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 |