| Title: | "Alkyl ether and enol ether analogs of (Z)-5-decenyl acetate, a pheromone component of the turnip moth,Agrotis segetum: probing a proposed bioactive conformation for chain-elongated analogs" |
| Author(s): | Gustavsson AL; Liljefors T; Hansson BS; |
| Address: | "Department of Organic Chemistry I Chemical Center, Lund University, P.O. Box 124, S-221 00, Lund, Sweden" |
| ISSN/ISBN: | 0098-0331 (Print) 0098-0331 (Linking) |
| Abstract: | "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 of1 and (Z)-5-dodecenyl acetate(2) have been synthesized and tested using singlecell electrophysiology. In these analogs a methylene group in positions 7 and 9 of1 and in positions 7 and 11 in2 have been replaced by an oxygen atom in order to energetically facilitate the formation of a loop conformation in the chain-elongated analogs.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 for2 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 of1 adopts a loop conformation in their bioactive conformations" |
| Notes: | "PubMed-not-MEDLINEGustavsson, A L Liljefors, T Hansson, B S eng 1995/06/01 J Chem Ecol. 1995 Jun; 21(6):815-32. doi: 10.1007/BF02033463" |
