ausblenden:
Schlagwörter:
lepidoptera
noctuidae
agrotis-segetum
(z)-5-decenyl acetate
pheromone analogs
structure-activity
chain-elongated analogs
enol
ethers
alkyl ethers
single-sensillum recordings
receptor interaction
molecular mechanics
mm2
mm3
single-sensillum recordings
sex-pheromone
molecular mechanics
carbocupration
lepidoptera
attractants
Zusammenfassung:
In order to test a previous conclusion that chain-elongated analogs of (Z)-5-decenyl acetate (1), a pheromone component of the turnip moth, Agrotis segetum, adopt a loop conformation of the terminal alkyl chain in the bioactive conformation, a series of alkyl ether and enol ether analogs of 1 and (Z)-5-dodecenyl acetate (2) have been synthesized and tested using single-cell electrophysiology. In these analogs a methylene group in positions 7 and 9 of 1 and in positions 7 and 11 in 2 have been replaced by an oxygen atom in order to energetically facilitate the formation of a loop conformation in the chain-elongated analogs. The electrophysiological results in combination with molecular mechanics (MM2 and MM3) calculated conformational energies show that the activity decreases of the chain-elongated ether analogs are significantly smaller than that for 2 and that these activity decreases parallel the conformational energies for a loop formation of the terminal chains in the analogs. The results support our previous conclusion that the terminal chain of chain-elongated analogs of 1 adopts a loop conformation in their bioactive conformations.
