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Chain-elongated analogues of a pheromone component of the turnip moth, Agrotis segetum. A structure-activity study using molecular mechanics

Liljefors, Tommy ; Thelin, Bernt ; Van Der Pers, Jan N.C. and Löfstedt, Christer LU (1985) In Journal of the Chemical Society, Perkin Transactions 2 p.1957-1962
Abstract

Chain-elongated analogues of (Z)-dec-5-enyl acetate, a pheromone component of the turnip moth, Agrotis segetum, have been studied. The conformational energies required for the analogues to mimic spatial relationships in the parent molecule, assumed to be crucial for the receptor interaction, were calculated by molecular mechanics (MM2). The calculated energies show a striking correlation with measured single-cell electrophysiological activities. The results indicate that an elongated alkyl chain is conformationally rearranged when the analogue is bound to the receptor, and that the biological activity is determined by the corresponding conformational energy.

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author
; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of the Chemical Society, Perkin Transactions 2
issue
12
pages
1957 - 1962
publisher
Royal Society of Chemistry
external identifiers
  • scopus:37049092024
ISSN
1472-779X
DOI
10.1039/P29850001957
project
Evolutionary mechanisms of pheromone divergence in Lepidoptera
language
English
LU publication?
yes
id
935dfc8b-2952-45ed-bb1e-dff0265bbb6e
date added to LUP
2020-07-23 15:40:54
date last changed
2020-09-23 15:07:20
@article{935dfc8b-2952-45ed-bb1e-dff0265bbb6e,
  abstract     = {<p>Chain-elongated analogues of (Z)-dec-5-enyl acetate, a pheromone component of the turnip moth, Agrotis segetum, have been studied. The conformational energies required for the analogues to mimic spatial relationships in the parent molecule, assumed to be crucial for the receptor interaction, were calculated by molecular mechanics (MM2). The calculated energies show a striking correlation with measured single-cell electrophysiological activities. The results indicate that an elongated alkyl chain is conformationally rearranged when the analogue is bound to the receptor, and that the biological activity is determined by the corresponding conformational energy.</p>},
  author       = {Liljefors, Tommy and Thelin, Bernt and Van Der Pers, Jan N.C. and Löfstedt, Christer},
  issn         = {1472-779X},
  language     = {eng},
  month        = {12},
  number       = {12},
  pages        = {1957--1962},
  publisher    = {Royal Society of Chemistry},
  series       = {Journal of the Chemical Society, Perkin Transactions 2},
  title        = {Chain-elongated analogues of a pheromone component of the turnip moth, Agrotis segetum. A structure-activity study using molecular mechanics},
  url          = {http://dx.doi.org/10.1039/P29850001957},
  doi          = {10.1039/P29850001957},
  year         = {1985},
}