4.2.3.63: (+)-cubenene synthase
This is an abbreviated version!
For detailed information about (+)-cubenene synthase, go to the full flat file.
Reaction
ECTree
4.2.3.63 (+)-cubenene synthaseAdvanced search results
results (
results (Natural Substrates Products
Natural Substrates Products on EC 4.2.3.63 - (+)-cubenene synthase
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
top
NATURAL SUBSTRATE 
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(2E,6E)-farnesyl diphosphate
(+)-cubenene + diphosphate
-
specific substrate
-
-
?
(2E,6E)-farnesyl diphosphate
(+)-cubenene + diphosphate
-
specific substrate
-
-
?
(2E,6E)-farnesyl diphosphate + H2O
(+)-epicubenol + diphosphate
-
specific substrate
reaction proceeds via 1,2- and 1,3-hydride shifts. (3R)-nerolidyl diphosphate is an intermediate in the cyclization. The initial isomerization of farnesyl diphosphate to (3R)-nerolidyl diphosphate takes place with suprafacial stereochemistry. Ionization of (3R)-nerolidyl diphosphate and attack by the 10-11 double bond on the re face of the cisoid allylic cation-diphosphate anion pair generates the cis-germacradienyl cation. A second electrophilic cyclization gives the cadinanyl cation, which upon a 1.2-hydride shift and syn capture of water generates epicubenol
-
?
(2E,6E)-farnesyl diphosphate + H2O
(+)-epicubenol + diphosphate
-
specific substrate
reaction proceeds via 1,2- and 1,3-hydride shifts. (3R)-nerolidyl diphosphate is an intermediate in the cyclization. The initial isomerization of farnesyl diphosphate to (3R)-nerolidyl diphosphate takes place with suprafacial stereochemistry. Ionization of (3R)-nerolidyl diphosphate and attack by the 10-11 double bond on the re face of the cisoid allylic cation-diphosphate anion pair generates the cis-germacradienyl cation. A second electrophilic cyclization gives the cadinanyl cation, which upon a 1.2-hydride shift and syn capture of water generates epicubenol
-
?
