Abstract:
:The enantiomers of analogs of (Z)-5-decenyl acetate, a pheromone component ofAgrotis segetum, substituted by a methyl group in the 2, 3, 4, 7, and 8 positions and dimethyl substituted in the 4,7 positions, have been synthesized and studied by an electrophysiological single-cell technique and by molecular mechanics calculations. The results demonstrate that the electrophysiological activity as well as the ability of the (Z)-5-decenyl acetate receptor to differentiate between enantiomers depends on the position of the methyl substituent. For analogs methyl substituted in the 2, 4, or 8 position, no differences in the activities of the enantiomers could be observed. In contrast, the enantiomers of the 3- and 7-methyl analogs display a significant difference in the activities, theR-enantiomers being more active than theS-enantiomers. From an analysis of the structure-activity results of the enantiomers of the 4,7-dimethyl-substituted analogs, the chiral sense of the alkylchain of the natural pheromone component on binding to its receptor could be deduced.
journal_name
J Chem Ecoljournal_title
Journal of chemical ecologyauthors
Jönsson S,Malmström T,Liljefors T,Hansson BSdoi
10.1007/BF00994319subject
Has Abstractpub_date
1993-03-01 00:00:00pages
459-84issue
3eissn
0098-0331issn
1573-1561journal_volume
19pub_type
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