4.2.3.64: (+)-epicubenol synthase
This is an abbreviated version!
For detailed information about (+)-epicubenol synthase, go to the full flat file.
Reaction
Synonyms
gecA, SGR_6065
ECTree
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Natural Substrates Products
Natural Substrates Products on EC 4.2.3.64 - (+)-epicubenol synthase
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REACTION DIAGRAM
(+)-epicubenol + diphosphate
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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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?
(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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?