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Literature summary for 4.2.3.53 extracted from

  • Sallaud, C.; Rontein, D.; Onillon, S.; Jabe, F.; Duffé, P.; Giacalone, C.; Thoraval, S.; Escoffier, C.; Herbette, G.; Leonhardt, N.; Causse, M.; Tissier, A.
    A novel pathway for sesquiterpene biosynthesis from Z,Z-farnesyl pyrophosphate in the wild tomato Solanum habrochaites (2009), Plant Cell, 21, 301-317.
    View publication on PubMedView publication on EuropePMC
Search for more literature for 4.2.3.53

Cloned(Commentary)

Cloned (Comment) Organism
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/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
(2Z,6Z)-farnesyl diphosphate Solanum habrochaites involved in sesquiterpene biosynthesis. The enzyme synthesizes a mixture of sesquiterpenoids from (2Z,6Z)-farnesyl 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 (+)-endo-beta-bergamotene + diphosphate
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Organism

Organism UniProt Comment Textmining
Solanum habrochaites B8XA41
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Purification (Commentary)

Purification (Comment) Organism
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 Solanum habrochaites

Reaction

Reaction Comment Organism Reaction ID
(2Z,6Z)-farnesyl diphosphate = (+)-endo-beta-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
a

Source Tissue

Source Tissue Comment Organism Textmining
leaf
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 Solanum habrochaites
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Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(2Z,6Z)-farnesyl diphosphate involved in sesquiterpene biosynthesis. The enzyme synthesizes a mixture of sesquiterpenoids from (2Z,6Z)-farnesyl 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 (+)-endo-beta-bergamotene + diphosphate
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 ?
(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 (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 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-beta-bergamotene + diphosphate
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 ?
additional information the enzyme is able to use neryl diphosphate and transform it into a product whose mass spectrum matches that of alpha-terpineol Solanum habrochaites ?
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Synonyms

Synonyms Comment Organism
SBS
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 Solanum habrochaites