Information on EC 4.2.3.50 - (+)-alpha-santalene synthase [(2Z,6Z)-farnesyl diphosphate cyclizing]

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The expected taxonomic range for this enzyme is: Solanum habrochaites

EC NUMBER
COMMENTARY
4.2.3.50
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RECOMMENDED NAME
GeneOntology No.
(+)-alpha-santalene synthase [(2Z,6Z)-farnesyl diphosphate cyclizing]
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(2Z,6Z)-farnesyl diphosphate = (+)-alpha-santalene + diphosphate
show the reaction diagram
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
B8XA41
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
santalene biosynthesis I
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Sesquiterpenoid and triterpenoid biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
(2Z,6Z)-farnesyl diphosphate lyase [cyclizing; (+)-alpha-santalene-forming]
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 (EC 4.2.3.50), while the (6S)-bisabolyl cation will give rise to (+)-endo-beta-bergamotene (see EC 4.2.3.53) as well as (-)-endo-alpha-bergamotene (see EC 4.2.3.54). 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 [1].
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(2Z,6Z)-farnesyl diphosphate
(+)-alpha-santalene + diphosphate
show the reaction diagram
B8XA41
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
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?
(2Z,6Z)-farnesyl diphosphate
(+)-alpha-santalene + (+)-endo-beta-bergamotene + (-)-endo-alpha-bergamotene + (-)-exo-alpha-bergamotene + (-)-epi-beta-santalene
show the reaction diagram
B8XA41
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
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additional information
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B8XA41
the enzyme is able to use neryl diphosphate and transform it into a product whose mass spectrum matches that of alpha-terpineol
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(2Z,6Z)-farnesyl diphosphate
(+)-alpha-santalene + diphosphate
show the reaction diagram
B8XA41
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
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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
B8XA41