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  • 1
    ISSN: 1573-1561
    Keywords: Structure-activity ; single-sensillum recordings ; receptor interaction ; pheromone ; (Z)-5-decenyl acetate ; alkenyl cuprate ; alkyl substitution ; Agrotis segetum ; Lepidotera ; Noctuidae
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Structure-activity relationships for 6-, 7-, 8-, and 9-alkyl substituted analogs of (Z)-5-decenyl acetate, a pheromone component of the turnip moth,Agrotis segetum, have been studied by electrophysiological single-sensillum recordings, and interpreted in terms of a receptor-interaction model. The compounds were prepared by alkenyl cuprate reactions withα,β-unsaturated carbonyl derivatives or alkyl halides. The electrophysiological results indicate steric repulsive interactions between the alkyl groups and the receptor in all the positions studied. This demonstrates a high complementarity between the receptor and the terminal alkyl chain.
    Type of Medium: Electronic Resource
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  • 2
    Electronic Resource
    Electronic Resource
    Springer
    Journal of chemical ecology 13 (1987), S. 2023-2040 
    ISSN: 1573-1561
    Keywords: Structure-activity ; conformational energy ; molecular mechanics ; double-bond configuration ; Agrotis segetum ; Lepidoptera ; Noctuidae ; sex pheromone ; single-cell recordings ; receptor interaction
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The dependence of the electrophysiological activity on the change of double-bond configuration of (Z)-5-decenyl acetate, a pheromone component of the turnip moth,Agrotis segetum, and a dienic analog, (E)-2,(Z)-5-decadienyl acetate, have been investigated by single-cell measurements and molecular mechanics calculations (MM2). A previously reported model for the interaction between a moth sex pheromone component and its receptor has been refined. This new model gives an essentially quantitative correlation between the measured activities and the calculated conformational energies for a biologically active conformation defined by the model. Previously obtained structure-activity results for chain-elongated analogs of (Z)-5-decenyl acetate are significantly improved by the refined model. The effect of a change of the double-bond configuration on the substrate-receptor interaction is not additive but depends on the conformational properties of the entire molecule.
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  • 3
    ISSN: 1573-1561
    Keywords: Structure-activity ; single-cell recordings ; receptor interaction ; (Z)-5-decenyl acetate ; chain-shortened analogs ; volatility ; vapor pressure ; Agrotis segetum ; Lepidoptera ; Noctuidae
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Structure-activity relationships for chain-shortened analogs of (Z)-5-decenyl acetate, a pheromone component of the turnip moth,Agrotis segetum, have been studied by electrophysiological single-sensillum technique and interpreted in terms of a previously reported receptor-interaction model. The results indicate that the terminal methyl group, as well as the acetate group, interacts with highly complementary receptor sites. The terminal alkyl chain is suggested to interact with a hydrophobic “pocket” extending over the two methylene groups closest to the terminal methyl group. The amounts of stimulus actually released from the odor source have been studied. The results demonstrate the necessity to take differences of volatility into account in comparisons of electrophysiological data for compounds of different chain lengths. It is shown that relative vapor pressures may to a good approximation be employed to estimate correction factors.
    Type of Medium: Electronic Resource
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