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Literature summary for 4.2.3.64 extracted from

  • Cane, D.; Tandon, M.
    Epicubenol synthase and the stereochemistry of the enzymatic cyclization of farnesyl and nerolidyl diphosphate (1995), J. Am. Chem. Soc., 117, 5602-5603.
No PubMed abstract available

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
(2E,6E)-farnesyl diphosphate + H2O Streptomyces sp. specific substrate (+)-epicubenol + diphosphate 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 Streptomyces sp. LL-B7 specific substrate (+)-epicubenol + diphosphate 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 ?

Organism

Organism UniProt Comment Textmining
Streptomyces sp.
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-
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Streptomyces sp. LL-B7
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-
-

Reaction

Reaction Comment Organism Reaction ID
(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 Streptomyces sp.

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(2E,6E)-farnesyl diphosphate + H2O specific substrate Streptomyces sp. (+)-epicubenol + diphosphate 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 specific substrate Streptomyces sp. LL-B7 (+)-epicubenol + diphosphate 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 ?