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Literature summary for 4.2.3.77 extracted from

  • Schmidt, C.O.; Bouwmeester, H.J.; Franke, S.; Konig, W.A.
    Mechanisms of the biosynthesis of sesquiterpene enantiomers (+)- and (-)-germacrene D in Solidago canadensis (1999), Chirality, 11, 353-362.
No PubMed abstract available
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Organism

Organism UniProt Comment Textmining
Solidago canadensis
-
-
-

Purification (Commentary)

Purification (Comment) Organism
-
 Solidago canadensis

Reaction

Reaction Comment Organism Reaction ID
(2E,6E)-farnesyl diphosphate = (+)-germacrene D + diphosphate the initial step is abstraction of the diphosphate moiety under ring closure to yield germacrenyl cation. The next step is a 1,2-hydride shift of H-7 into the isopropyl group, generating a germacrenyl cation with the positive charge at position 7. The cation undergoes a 1,2-hydride shift of H-6 yielding a cation with positive charge at position 6. During this step the configuration at C-7 is fixed. Finally, the cation is deprotonated at C-15 and the positive charge is quenched by two electron pair shifts to generate (+)-germacrene D Solidago canadensis
a

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(2E,6E)-farnesyl diphosphate
-
 Solidago canadensis (+)-germacrene D + diphosphate
-
 ?