Cloned (Comment) | Organism |
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cloned in a bacterial expression vector with a polyhistidine tag located at the C-terminus of the protein. Expression of Z,Z-farnesyl diphosphate synthase and SBS in tobacco trichomes leads to the production of tomato class II sesquiterpenes | Solanum habrochaites |
Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
---|---|---|---|---|---|---|
(2Z,6Z)-farnesyl diphosphate | Solanum habrochaites | sesquiterpene biosynthesis | (-)-endo-alpha-bergamotene + diphosphate | - |
? |
Organism | UniProt | Comment | Textmining |
---|---|---|---|
Solanum habrochaites | B8XA41 | - |
- |
Purification (Comment) | Organism |
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- |
Solanum habrochaites |
Reaction | Comment | Organism | Reaction ID |
---|---|---|---|
(2Z,6Z)-farnesyl diphosphate = (-)-endo-alpha-bergamotene + diphosphate | following dephosphorylation of (2Z,6Z)-farnesyl diphosphate, the (2Z,6Z)-farnesyl carbocation is converted to either the (6R)- or the (6S)-bisabolyl cations depending on the stereochemistry of the 6,1 closure. The (6R)-bisabolyl cation will then lead to the formation of (+)-alpha-santalene, while the (6S)-bisabolyl cation will give rise to (-)-endo-alpha-bergamotene and (+)-endo-beta-bergamotene. Small amounts of (-)-epi-beta-santalene are also formed from the (6R)-bisabolyl cation and small amounts of (-)-exo-alpha-bergamotene are formed from the (6S)-bisabolyl cation | Solanum habrochaites |
Source Tissue | Comment | Organism | Textmining |
---|---|---|---|
leaf | - |
Solanum habrochaites | - |
Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
---|---|---|---|---|---|---|
(2Z,6Z)-farnesyl diphosphate | sesquiterpene biosynthesis | Solanum habrochaites | (-)-endo-alpha-bergamotene + diphosphate | - |
? | |
(2Z,6Z)-farnesyl diphosphate | because (2Z,6Z)-farnesyl diphosphate is not commercially available, in vitro enzymatic assays with both (2Z,6Z)-farnesyl diphosphate synthase and and SBS recombinant proteins are conducted using isopentenyl diphosphate and dimethylallyl diphosphate as substrates. No activity with geranyl diphosphate, (2E,6E)-farnesyl diphosphate, and (2E,6E,10E)-geranylgeranyl diphosphate. Multiproduct cyclization pathway for the cyclization of (2Z,6Z)-farnesyl diphosphate to class II sesquiterpenes by SBS: following dephosphorylation of (2Z,6Z)-farnesyl diphosphate, the Z,Z-farnesyl carbocation is converted to either the (6R)- or the (6S)-bisabolyl cations depending on the stereochemistry of the 6,1 closure. The (6R)-bisabolyl cation will then lead to the formation of (+)-alpha-santalene and (-)-epi-beta-santalene, while the (6S)-bisabolyl cation will give rise to (-)-exo-alpha-bergamotene, (-)-endo-alpha-bergamotene, and (+)-endo-beta-bergamotene | Solanum habrochaites | (-)-endo-alpha-bergamotene + diphosphate | - |
? | |
additional information | the enzyme is able to use neryl diphosphate and transform it into a product whose mass spectrum matches that of alphs-terpineol | Solanum habrochaites | ? | - |
? |
Synonyms | Comment | Organism |
---|---|---|
SBS | - |
Solanum habrochaites |