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(2E,6E)-farnesyl diphosphate + H2O = (+)-epicubenol + diphosphate
(2E,6E)-farnesyl diphosphate + H2O = (+)-epicubenol + diphosphate
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-
-
-
(2E,6E)-farnesyl diphosphate + H2O = (+)-epicubenol + diphosphate
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
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(2E,6E)-farnesyl diphosphate + H2O = (+)-epicubenol + diphosphate
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
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-
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(2E,6E)-farnesyl diphosphate + H2O
(+)-epicubenol + diphosphate
(2E,6E)-farnesyl diphosphate + H2O
(+)-epicubenol + diphosphate
-
specific substrate
(+)-cubenene synthase and (+)-epicubenol synthase are dual functions of the same enzyme
-
?
(2E,6E)-farnesyl diphosphate + H2O
(+)-epicubenol + diphosphate
-
specific substrae
reaction proceeds via 1,2- and 1,3-hydride shifts
-
?
(2E,6E)-farnesyl diphosphate + H2O
(+)-epicubenol + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + H2O
(+)-epicubenol + diphosphate
-
-
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
(+)-epicubenol + diphosphate
-
-
reaction proceeds via 1,2-hydride shift
-
?
(2E,6E)-farnesyl diphosphate + H2O
(+)-epicubenol + diphosphate
-
-
the hydroxyl oxygen atom derives exclusively from water
-
?
(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
-
-
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
(+)-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
-
-
the hydroxyl oxygen atom derives exclusively from water
-
?
(2E,6E)-farnesyl diphosphate + H2O
(+)-epicubenol + diphosphate
-
-
reaction proceeds via 1,2-hydride shift
-
?
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(2E,6E)-farnesyl diphosphate + H2O
(+)-epicubenol + diphosphate
(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
-
?
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Cane, D.E.; Ke, N.
Epicubenol synthase. Origin of the oxygen atom of a bacterial sesquiterpene alcohol
Bioorg. Med. Chem. Lett.
10
105-107
2000
Streptomyces sp., Streptomyces sp. LL-B7
brenda
Cane, D.; Tandon, M.; Prabhakaran, P.
Epicubenol synthase and the enzymatic cyclization of farnesyl diphosphate
J. Am. Chem. Soc.
115
8103-8106
1993
Streptomyces sp., Streptomyces sp. LL-B7
-
brenda
Cane, D.; Tandon, M.
Epicubenol synthase and the stereochemistry of the enzymatic cyclization of farnesyl and nerolidyl diphosphate
J. Am. Chem. Soc.
117
5602-5603
1995
Streptomyces sp., Streptomyces sp. LL-B7
-
brenda
Nabeta, K.; Kigure, K.; Fujita, M.; Nagoya, T.; Ishikawa, T.; Okuyama, H.; Takasawa, T.
Biosynthesis of (+)-cubenene and (+)-epicubenol by cell-free extracts of cultured cells of Heteroscyphus planus and cyclization of [ 2H]farnesyl diphosphates
J. Chem. Soc.
1
1935-1939
1995
Heteroscyphus planus
-
brenda
Nabeta, K.; Fujita, M.; Komuro, K.; Katayama, K.; Takasawa, T.
In vitro biosynthesis of cadinanes by cell-free extracts of cultured cells of Heteroscyphus planus
J. Chem. Soc.
1
2065-2070
1997
Heteroscyphus planus
-
brenda
Cane, D.; Tandon, M.
Biosynthesis of (+)-epicubenol
Tetrahedron Lett.
35
5355-5358
1994
Streptomyces sp., Streptomyces sp. LL-B7
-
brenda
Nakano, C.; Tezuka, T.; Horinouchi, S.; Ohnishi, Y.
Identification of the SGR6065 gene product as a sesquiterpene cyclase involved in (+)-epicubenol biosynthesis in Streptomyces griseus
J. Antibiot.
65
551-558
2012
Streptomyces griseus (B1W477), Streptomyces griseus
brenda