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  • 1
    Electronic Resource
    Electronic Resource
    Replacement of the terminal methyl group in a moth sex pheromone component by a halogen atom: Hydrophobicity and size effects on electrophysiological single-cell activities (1991)
    Springer
    Journal of chemical ecology 17 (1991), S. 1381-1397 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; noctuidae ; Agrotis segetum ; (Z)-5-decenyl acetate ; pheromone analogue ; halides ; structure-activity ; single-sensillum ; recordings ; receptor-interaction
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Analogs of (Z)-5-decenyl acetate, a pheromone component of the turnip moth,Agrotis segetum, with a chloro, bromo, or iodo substituent in place of the terminal methyl group have been synthesized and tested by electrophysiological single-sensillum recordings. The electrophysiological results have been interpreted in terms of substituent size and hydrophobicity. Interaction energies based on receptor interaction models have been calculated using the molecular mechanics [MM2(85)] method. The results support our previously suggested receptor interaction model in which the terminal alkyl chain interact with a complementary hydrophobic receptor “pocket” with very limited flexibility.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00983771
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  • 2
    Electronic Resource
    Electronic Resource
    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 (1995)
    Springer
    Journal of chemical ecology 21 (1995), S. 815-832 
    Details
    ISSN: 1573-1561
    Keywords: 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
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: 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.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02033463
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  • 3
    Electronic Resource
    Electronic Resource
    Enantiomers of methyl substituted analogs of (Z)-5-decenyl acetate as probes for the chirality and complementarity of its receptor inAgrotis segetum 1: Synthesis and structure-activity relationships (1993)
    Springer
    Journal of chemical ecology 19 (1993), S. 459-484 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Noctuidae ; Agrotis segetum ; (Z)-5-decenyl acetate ; pheromone analog ; methyl substitution ; structure-activity ; single-sensillum recordings ; receptor interaction ; conformational analysis ; molecular mechanics ; enantiomers ; chirality
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: 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.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00994319
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  • 4
    Electronic Resource
    Electronic Resource
    Introduction of methyl groups to acetate substituted chain of (Z)-5-decenyl acetate, a pheromone component of turnip moth,agrotis segetum: synthesis, single-sensillum recordings, and structure-activity relationships (1992)
    Springer
    Journal of chemical ecology 18 (1992), S. 637-657 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Noctuidae ; Agrotis segetum ; (Z)-5-decenyl acetate ; pheromone analog ; methyl substitution ; structure-activity ; single-sensillum recordings ; receptor interaction ; conformational analysis ; molecular mechanics
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Methyl-substituted analogs of (Z)-5-decenyl acetate, a pheromone component of the turnip moth,Agrotis segetum, have been synthesized and studied by electrophysiological single-sensillum recordings and molecular mechanics calculations [MM2(85)]. The analogs are monomethyl substituted in the 2, 3, 4, and 5 positions and geminally dimethyl substituted in the 2, 3, and 4 positions. The methyl groups have been employed as space probes to study the degree of steric complementarity between the acetate-substituted alkyl chain of the pheromone component and its receptor. The electrophysiological activities, interpreted in terms of a receptor interaction model, indicate significant steric repulsive interactions between the introduced methyl groups and the receptor. This implies a high degree of complementarity between the acetate-substituted alkyl chain of the natural pheromone component and its receptor.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00987825
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