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  • 1
    Electronic Resource
    Electronic Resource
    Alkyl substitution in terminal chain of (Z)-5-decenyl acetate, a pheromone component of turnip moth,Agrotis segetum. Synthesis, single-sensillum recordings, and structure-activity relationships (1991)
    Springer
    Journal of chemical ecology 17 (1991), S. 103-122 
    Details
    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
    URL: http://dx.doi.org/10.1007/BF00994425
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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
    Bioisosteric Approach to Elucidation of Binding of the Acetate Group of a Moth Sex Pheromone Component to Its Receptor (1997)
    Springer
    Journal of chemical ecology 23 (1997), S. 2755-2776 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Noctuidae ; Agrotis segetum ; (Z)-5-decenyl acetate ; pheromone analogs ; structure–activity ; bioisosteres ; single-sensillum recordings ; receptor interaction ; molecular electrostatic potential ; quantum mechanical calculations ; ab initio calculations
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract A number of analogs of (Z)-5-decenyl acetate, a pheromone component of the turnip moth,Agrotis segetum, in which the acetate group has been replaced by functional groups that may function as bioisosters, have been synthesized and tested using single-cell electrophysiology. The activities have been interpreted in terms of the molecular electrostatic potentials of the polar functional group as calculated byab initio quantum mechanical calculations. It is concluded that both oxygens of the acetate group in (Z)-5-decenyl acetate contribute to the interactions between the pheromone component and its receptor. Furthermore, the results indicate that the crucial interaction between the carbonyl group and the receptor, which is most probably a hydrogen bonding interaction, takes place in a direction pointing away from the hydrocarbon chain of the pheromone component.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1022563010599
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  • 4
    Electronic Resource
    Electronic Resource
    Effects of double-bond configuration on interaction between a moth sex pheromone component and its receptor (1987)
    Springer
    Journal of chemical ecology 13 (1987), S. 2023-2040 
    Details
    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.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01041729
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  • 5
    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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  • 6
    Electronic Resource
    Electronic Resource
    Structure-activity relationships for chain-shortened analogs of (Z)-5-decenyl acetate, a pheromone component of the turnip moth,Agrotis segetum (1990)
    Springer
    Journal of chemical ecology 16 (1990), S. 667-684 
    Details
    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
    URL: http://dx.doi.org/10.1007/BF01016478
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  • 7
    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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