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

This is an abbreviated version!
For detailed information about (+)-alpha-santalene synthase [(2Z,6Z)-farnesyl diphosphate cyclizing], go to the full flat file.

Reaction

(2Z,6Z)-farnesyl diphosphate
=
(+)-alpha-santalene
+
diphosphate

Synonyms

SBS

ECTree

     4 Lyases
         4.2 Carbon-oxygen lyases
             4.2.3 Acting on phosphates
                4.2.3.50 (+)-alpha-santalene synthase [(2Z,6Z)-farnesyl diphosphate cyclizing]

Substrates Products

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

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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(2Z,6Z)-farnesyl diphosphate
(+)-alpha-santalene + (+)-endo-beta-bergamotene + (-)-endo-alpha-bergamotene + (-)-exo-alpha-bergamotene + (-)-epi-beta-santalene
show the reaction diagram
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
-
-
?
(2Z,6Z)-farnesyl diphosphate
(+)-alpha-santalene + diphosphate
show the reaction diagram
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
-
-
?
additional information
?
-
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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-
?