Information on EC 4.2.3.63 - (+)-cubenene synthase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY
4.2.3.63
-
RECOMMENDED NAME
GeneOntology No.
(+)-cubenene synthase
-
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
(2E,6E)-farnesyl diphosphate = (+)-cubenene + diphosphate
show the reaction diagram
-
-
-
-
(2E,6E)-farnesyl diphosphate = (+)-cubenene + diphosphate
show the reaction diagram
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 = (+)-cubenene + diphosphate
show the reaction diagram
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
Streptomyces sp. LL-B7
-
-
SYSTEMATIC NAME
IUBMB Comments
(2E,6E)-farnesyl-diphosphate diphosphate-lyase [(+)-cubenene-forming]
Requires Mg2+.
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
bifunctional (+)-cubenene synthase and (+)-epicubenol synthase
-
-
Manually annotated by BRENDA team
Streptomyces sp. LL-B7
-
-
-
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(2E,6E)-farnesyl diphosphate + H2O
(+)-cubenene + diphosphate
show the reaction diagram
-
-
reaction proceeds via 1,3-hydride shift. (3R)-nerolidyl diphosphate is an intermediate in the cyclization. Cyclization of [ 13,13,13-2H3]farnesy1 diphosphate with crude epicubenol synthase gives [ 13,13,13-2H3]epicubenol
-
?
(2E,6E)-farnesyl diphosphate + H2O
(+)-cubenene + diphosphate
show the reaction diagram
-
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
(+)-cubenene + diphosphate
show the reaction diagram
-
specific substrae
(+)-cubenene synthase and (+)-epicubenol synthase are dual functions of the same enzyme
-
?
(2E,6E)-farnesyl diphosphate + H2O
(+)-cubenene + diphosphate
show the reaction diagram
-
specific substrae
reaction proceeds via 1,2- and 1,3-hydride shifts
-
?
(2E,6E)-farnesyl diphosphate + H2O
(+)-cubenene + diphosphate
show the reaction diagram
Streptomyces sp. LL-B7
-
-
reaction proceeds via 1,3-hydride shift. (3R)-nerolidyl diphosphate is an intermediate in the cyclization. Cyclization of [ 13,13,13-2H3]farnesy1 diphosphate with crude epicubenol synthase gives [ 13,13,13-2H3]epicubenol
-
?
(2E,6E)-farnesyl diphosphate + H2O
(+)-cubenene + diphosphate
show the reaction diagram
Streptomyces sp. LL-B7
-
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
show the reaction diagram
Streptomyces sp., Streptomyces sp. LL-B7
-
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
-
?
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(2E,6E)-farnesyl diphosphate + H2O
(+)-cubenene + diphosphate
show the reaction diagram
-
specific substrate
-
-
?
(2E,6E)-farnesyl diphosphate + H2O
(+)-epicubenol + diphosphate
show the reaction diagram
-
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
(+)-cubenene + diphosphate
show the reaction diagram
Streptomyces sp. LL-B7
-
specific substrate
-
-
?
(2E,6E)-farnesyl diphosphate + H2O
(+)-epicubenol + diphosphate
show the reaction diagram
Streptomyces sp. LL-B7
-
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
-
?
SPECIFIC ACTIVITY [µmol/min/mg]
SPECIFIC ACTIVITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
268
-
-
pH not specified in the publication, temperature not specified in the publication
Purification/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE