Information on EC 4.2.3.54 - (-)-endo-alpha-bergamotene synthase [(2Z,6Z)-farnesyl diphosphate cyclizing]

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The expected taxonomic range for this enzyme is: Solanum habrochaites

EC NUMBER
COMMENTARY hide
4.2.3.54
-
RECOMMENDED NAME
GeneOntology No.
(-)-endo-alpha-bergamotene synthase [(2Z,6Z)-farnesyl diphosphate cyclizing]
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(2Z,6Z)-farnesyl diphosphate = (-)-endo-alpha-bergamotene + diphosphate
show the reaction diagram
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
bergamotene biosynthesis II
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-
SYSTEMATIC NAME
IUBMB Comments
(2Z,6Z)-farnesyl diphosphate lyase (cyclizing; (-)-endo-alpha-bergamotene-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 (see EC 4.2.3.50), while the (6S)-bisabolyl cation will give rise to (+)-endo-beta-bergamotene (EC 4.2.3.53) as well as (-)-endo-alpha-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 [1].
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
SwissProt
Manually annotated by BRENDA team
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
(-)-endo-alpha-bergamotene + diphosphate
show the reaction diagram
additional information
?
-
the enzyme is able to use neryl diphosphate and transform it into a product whose mass spectrum matches that of alphs-terpineol
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NATURAL SUBSTRATES
NATURAL PRODUCTS
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
(-)-endo-alpha-bergamotene + diphosphate
show the reaction diagram
B8XA41
sesquiterpene biosynthesis
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-
?
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
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