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Information on EC 4.2.3.54 - (-)-endo-alpha-bergamotene synthase [(2Z,6Z)-farnesyl diphosphate cyclizing] and Organism(s) Solanum habrochaites and UniProt Accession B8XA41

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EC Tree
IUBMB Comments
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 .
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Solanum habrochaites
UNIPROT: B8XA41
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The taxonomic range for the selected organisms is: Solanum habrochaites
The enzyme appears in selected viruses and cellular organisms
Synonyms
SBS, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(2Z,6Z)-farnesyl diphosphate = (-)-endo-alpha-bergamotene + 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
PATHWAY SOURCE
PATHWAYS
-
-
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].
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 SUBSTRATE
NATURAL 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
sesquiterpene biosynthesis
-
-
?
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
SwissProt
Manually annotated by BRENDA team
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
SBS_SOLHA
777
0
90626
Swiss-Prot
Chloroplast (Reliability: 3)
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
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Sallaud, C.; Rontein, D.; Onillon, S.; Jabe, F.; Duff, 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
Plant Cell
21
301-317
2009
Solanum habrochaites (B8XA41)
Manually annotated by BRENDA team