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Literature summary 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

Cloned(Commentary)

EC Number Cloned (Comment) Organism
2.5.1.92 cloned in a bacterial expression vector with a poly-histidine tag located at the C terminus of the protein Solanum habrochaites
4.2.3.50 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
4.2.3.53 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
4.2.3.54 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

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
2.5.1.92 0.01
-
 dimethylallyl diphosphate pH 7.8, 30°C, 0.035 mM isopentenyl diphosphate Solanum habrochaites
2.5.1.92 0.01
-
 dimethylallyl diphosphate pH 7.8, 30°C, 0.18 mM isopentenyl diphosphate Solanum habrochaites
2.5.1.92 0.035
-
 dimethylallyl diphosphate pH 7.8, 30°C, 0.21 mM isopentenyl diphosphate Solanum habrochaites

Molecular Weight [Da]

EC Number Molecular Weight [Da] Molecular Weight Maximum [Da] Comment Organism
2.5.1.92 28000
-
 gel filtration Solanum habrochaites

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.5.1.92 dimethylallyl diphosphate + 2 isopentenyl diphosphate Solanum habrochaites
-
 2 diphosphate + (2Z,6Z)-farnesyl diphosphate
-
 ?
4.2.3.50 (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 (+)-alpha-santalene + diphosphate
-
 ?
4.2.3.53 (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
-
 ?
4.2.3.54 (2Z,6Z)-farnesyl diphosphate Solanum habrochaites sesquiterpene biosynthesis (-)-endo-alpha-bergamotene + diphosphate
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
2.5.1.92 Solanum habrochaites B8XA40
-
-
4.2.3.50 Solanum habrochaites B8XA41
-
-
4.2.3.53 Solanum habrochaites B8XA41
-
-
4.2.3.54 Solanum habrochaites B8XA41
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
2.5.1.92
-
 Solanum habrochaites
4.2.3.50
-
 Solanum habrochaites
4.2.3.53
-
 Solanum habrochaites
4.2.3.54
-
 Solanum habrochaites

Reaction

EC Number Reaction Comment Organism Reaction ID
4.2.3.50 (2Z,6Z)-farnesyl diphosphate = (+)-alpha-santalene + 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
4.2.3.53 (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
4.2.3.54 (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
a

Source Tissue

EC Number Source Tissue Comment Organism Textmining
2.5.1.92 leaf
-
 Solanum habrochaites
-
4.2.3.50 leaf
-
 Solanum habrochaites
-
4.2.3.53 leaf
-
 Solanum habrochaites
-
4.2.3.54 leaf
-
 Solanum habrochaites
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.5.1.92 dimethylallyl diphosphate + 2 isopentenyl diphosphate
-
 Solanum habrochaites 2 diphosphate + (2Z,6Z)-farnesyl diphosphate
-
 ?
2.5.1.92 dimethylallyl diphosphate + 2 isopentenyl diphosphate positive cooperativity for the binding of the enzyme to isopentenyl diphosphate Solanum habrochaites 2 diphosphate + (2Z,6Z)-farnesyl diphosphate
-
 ?
2.5.1.92 neryl diphosphate + isopentenyl diphosphate
-
 Solanum habrochaites diphosphate + (2Z,6Z)-farnesyl diphosphate
-
 ?
4.2.3.50 (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 (+)-alpha-santalene + diphosphate
-
 ?
4.2.3.50 (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 (+)-alpha-santalene + (+)-endo-beta-bergamotene + (-)-endo-alpha-bergamotene + (-)-exo-alpha-bergamotene + (-)-epi-beta-santalene
-
 ?
4.2.3.50 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 ?
-
 ?
4.2.3.53 (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
-
 ?
4.2.3.53 (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
-
 ?
4.2.3.53 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 ?
-
 ?
4.2.3.54 (2Z,6Z)-farnesyl diphosphate sesquiterpene biosynthesis Solanum habrochaites (-)-endo-alpha-bergamotene + diphosphate
-
 ?
4.2.3.54 (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
-
 ?
4.2.3.54 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 ?
-
 ?

Subunits

EC Number Subunits Comment Organism
2.5.1.92 monomer
-
 Solanum habrochaites

Synonyms

EC Number Synonyms Comment Organism
2.5.1.92 cis,cis-farnesyl diphosphate synthase
-
 Solanum habrochaites
2.5.1.92 Z,Z-farnesyl pyrophosphate synthase
-
 Solanum habrochaites
2.5.1.92 Z,Z-FPP synthase
-
 Solanum habrochaites
2.5.1.92 zFPS
-
 Solanum habrochaites
4.2.3.50 SBS
-
 Solanum habrochaites
4.2.3.53 SBS
-
 Solanum habrochaites
4.2.3.54 SBS
-
 Solanum habrochaites