EC Number |
Substrates |
Organism |
Products |
Reversibility |
---|
4.2.3.64 | (2E,6E)-farnesyl diphosphate + H2O |
- |
Streptomyces griseus |
(+)-epicubenol + diphosphate |
- |
? |
4.2.3.64 | (2E,6E)-farnesyl diphosphate + H2O |
- |
Streptomyces sp. |
(+)-epicubenol + diphosphate |
reaction proceeds via 1,3-hydride shift. (3R)-nerolidyl diphosphate is an intermediate in the cyclization. Cyclization of [ 13,13,13-2H3]farnesy1 diphosphate with crude epicubenol synthase gives [ 13,13,13-2H3]epicubenol |
? |
4.2.3.64 | (2E,6E)-farnesyl diphosphate + H2O |
- |
Streptomyces sp. |
(+)-epicubenol + diphosphate |
reaction proceeds via 1,2-hydride shift |
? |
4.2.3.64 | (2E,6E)-farnesyl diphosphate + H2O |
- |
Streptomyces sp. |
(+)-epicubenol + diphosphate |
the hydroxyl oxygen atom derives exclusively from water |
? |
4.2.3.64 | (2E,6E)-farnesyl diphosphate + H2O |
specific substrate |
Heteroscyphus planus |
(+)-epicubenol + diphosphate |
(+)-cubenene synthase and (+)-epicubenol synthase are dual functions of the same enzyme |
? |
4.2.3.64 | (2E,6E)-farnesyl diphosphate + H2O |
specific substrate |
Streptomyces sp. |
(+)-epicubenol + diphosphate |
reaction proceeds via 1,2- and 1,3-hydride shifts. (3R)-nerolidyl diphosphate is an intermediate in the cyclization. The initial isomerization of farnesyl diphosphate to (3R)-nerolidyl diphosphate takes place with suprafacial stereochemistry. Ionization of (3R)-nerolidyl diphosphate and attack by the 10-11 double bond on the re face of the cisoid allylic cation-diphosphate anion pair generates the cis-germacradienyl cation. A second electrophilic cyclization gives the cadinanyl cation, which upon a 1.2-hydride shift and syn capture of water generates epicubenol |
? |
4.2.3.64 | (2E,6E)-farnesyl diphosphate + H2O |
specific substrae |
Heteroscyphus planus |
(+)-epicubenol + diphosphate |
reaction proceeds via 1,2- and 1,3-hydride shifts |
? |
4.2.3.64 | (2E,6E)-farnesyl diphosphate + H2O |
- |
Streptomyces sp. LL-B7 |
(+)-epicubenol + diphosphate |
reaction proceeds via 1,3-hydride shift. (3R)-nerolidyl diphosphate is an intermediate in the cyclization. Cyclization of [ 13,13,13-2H3]farnesy1 diphosphate with crude epicubenol synthase gives [ 13,13,13-2H3]epicubenol |
? |
4.2.3.64 | (2E,6E)-farnesyl diphosphate + H2O |
specific substrate |
Streptomyces sp. LL-B7 |
(+)-epicubenol + diphosphate |
reaction proceeds via 1,2- and 1,3-hydride shifts. (3R)-nerolidyl diphosphate is an intermediate in the cyclization. The initial isomerization of farnesyl diphosphate to (3R)-nerolidyl diphosphate takes place with suprafacial stereochemistry. Ionization of (3R)-nerolidyl diphosphate and attack by the 10-11 double bond on the re face of the cisoid allylic cation-diphosphate anion pair generates the cis-germacradienyl cation. A second electrophilic cyclization gives the cadinanyl cation, which upon a 1.2-hydride shift and syn capture of water generates epicubenol |
? |
4.2.3.64 | (2E,6E)-farnesyl diphosphate + H2O |
- |
Streptomyces sp. LL-B7 |
(+)-epicubenol + diphosphate |
the hydroxyl oxygen atom derives exclusively from water |
? |