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A mapping of the interactions between a moth sex pheromone component and its receptor

Gustavsson, Anna-Lena (1996)
Abstract (Swedish)
Popular Abstract in Swedish

Insekter kommunicerar med dofter. De artspecifika kemiska substanser som används mellan individer kallas feromoner. Hos sädesbroddflyet, Agrotis segetum, producerar honan en "parfym", ett sexualferomon som består av flera komponenter, för att locka till sig en hane. På hanens antenner finns lukthår med särskilda motagare, receptorer, som används för att detektera honans parfym.



En av sädesbroddflyets sexualferomonkomponenter, (Z)-5-decenylacetat, och dess receptor har studerats i detta arbete. Eftersom den tre-dimensionella strukturen av receptorn inte är känd har strukturanaloger till den naturliga komponenten syntetiserats och deras biologiska aktivitet mätts. Med... (More)
Popular Abstract in Swedish

Insekter kommunicerar med dofter. De artspecifika kemiska substanser som används mellan individer kallas feromoner. Hos sädesbroddflyet, Agrotis segetum, producerar honan en "parfym", ett sexualferomon som består av flera komponenter, för att locka till sig en hane. På hanens antenner finns lukthår med särskilda motagare, receptorer, som används för att detektera honans parfym.



En av sädesbroddflyets sexualferomonkomponenter, (Z)-5-decenylacetat, och dess receptor har studerats i detta arbete. Eftersom den tre-dimensionella strukturen av receptorn inte är känd har strukturanaloger till den naturliga komponenten syntetiserats och deras biologiska aktivitet mätts. Med molekylmekanik och ab initio beräkningar har information om analogernas molekylära egenskaper, som geometrier, konformations- energier och elektrostatiska egenskaper, erhållits. Utifrån dessa resultat kan man förstå hur (Z)-5-decenylacetat och dess receptor interagerar.



Målet med dessa struktur-aktivitetsstudier har varit att bestämma den biologiskt aktiva konformationen av den naturliga feromonkomponenten samt receptorns kirala igenkänning. Den biologiskt aktiva konformationen hos kedjeförlängda analoger har studerats. Vidare har den polära gruppen, esterfunktionen, hos den naturliga feromonkomponenten och dess samverkan med receptorn undersökts. Slutligen har 3D-QSAR- metodologin använts för att utveckla en kvantitativ modell för sambandet mellan biologisk aktivitet och molekylära/strukturella egenskaper hos ett stort antal analoger till den naturliga feromonkomponenten. (Less)
Abstract
A number of analogues of (Z)-5-decenyl acetate (1), a pheromone component of the turnip moth, Agrotis segetum, have been synthesised and tested by using single-cell electrophysiology, in order to investigate the relationships between structure and activity, and to elucidate the interactions between 1 and its receptor. Molecular mechanics and ab initio quantum mechanical calculations have been used to provide information on molecular properties, conformational energies and electrostatic potentials, which have been used in the interpretation of the observed activities.



A study of alkyl ether and enol ether analogues of 1 and (Z)-5-dodecenyl acetate (2) provides support for a previous hypothesis that the terminal chain of... (More)
A number of analogues of (Z)-5-decenyl acetate (1), a pheromone component of the turnip moth, Agrotis segetum, have been synthesised and tested by using single-cell electrophysiology, in order to investigate the relationships between structure and activity, and to elucidate the interactions between 1 and its receptor. Molecular mechanics and ab initio quantum mechanical calculations have been used to provide information on molecular properties, conformational energies and electrostatic potentials, which have been used in the interpretation of the observed activities.



A study of alkyl ether and enol ether analogues of 1 and (Z)-5-dodecenyl acetate (2) provides support for a previous hypothesis that the terminal chain of chain-elongated analogues of 1 adopts a loop conformation in their bioactive conformations.



The acetate group of 1 has been replaced by various functional groups, which may serve as bioisosteres, to elucidate how and in what directions the acetate group interacts with the receptor site.



A quantitative model, for the relationship between the activity for a large number of analogues of 1 and the structural characteristics of the analogues, was developed by using three-dimensional quantitative structure-activity relationship (3D-QSAR) methodology, including partial least square (PLS) analyses.



The bioactive conformation of 1, a cisoid conformation, and the chiral recognition of the receptor was probed using constrained analogues, the enantiomers of cis- and trans-3-(4-propyl-cyclopent-2-enyl) propyl acetate. (Less)
Please use this url to cite or link to this publication:
author
opponent
  • Dr Björkling, Fredrik, Leo Pharmaceutical Products, Denmark
publishing date
type
Thesis
publication status
published
subject
keywords
Organic chemistry, chiral recognition, bioactive conformation, structure-activity, Agrotis segetum, (Z)-5-decenyl acetate, pheromone analogues, single-cell electrophysiology, molecular mechanics, ab initio, MM3, quantum mechanical calculations, 3D-QSAR, bioisosteres, Organisk kemi
pages
71 pages
publisher
Organic Chemistry, Lund University
defense location
Center for Chemistry, lecture hall D
defense date
1996-12-06 10:15
external identifiers
  • Other:ISRN: LUNDL/NKOK-1035-SE
ISBN
91-628-2253-5
language
English
LU publication?
no
id
5f631318-fc87-49a8-a6bb-423aa62179f1 (old id 28828)
date added to LUP
2007-06-12 12:07:53
date last changed
2016-09-19 08:45:08
@misc{5f631318-fc87-49a8-a6bb-423aa62179f1,
  abstract     = {A number of analogues of (Z)-5-decenyl acetate (1), a pheromone component of the turnip moth, Agrotis segetum, have been synthesised and tested by using single-cell electrophysiology, in order to investigate the relationships between structure and activity, and to elucidate the interactions between 1 and its receptor. Molecular mechanics and ab initio quantum mechanical calculations have been used to provide information on molecular properties, conformational energies and electrostatic potentials, which have been used in the interpretation of the observed activities.<br/><br>
<br/><br>
A study of alkyl ether and enol ether analogues of 1 and (Z)-5-dodecenyl acetate (2) provides support for a previous hypothesis that the terminal chain of chain-elongated analogues of 1 adopts a loop conformation in their bioactive conformations.<br/><br>
<br/><br>
The acetate group of 1 has been replaced by various functional groups, which may serve as bioisosteres, to elucidate how and in what directions the acetate group interacts with the receptor site.<br/><br>
<br/><br>
A quantitative model, for the relationship between the activity for a large number of analogues of 1 and the structural characteristics of the analogues, was developed by using three-dimensional quantitative structure-activity relationship (3D-QSAR) methodology, including partial least square (PLS) analyses.<br/><br>
<br/><br>
The bioactive conformation of 1, a cisoid conformation, and the chiral recognition of the receptor was probed using constrained analogues, the enantiomers of cis- and trans-3-(4-propyl-cyclopent-2-enyl) propyl acetate.},
  author       = {Gustavsson, Anna-Lena},
  isbn         = {91-628-2253-5},
  keyword      = {Organic chemistry,chiral recognition,bioactive conformation,structure-activity,Agrotis segetum,(Z)-5-decenyl acetate,pheromone analogues,single-cell electrophysiology,molecular mechanics,ab initio,MM3,quantum mechanical calculations,3D-QSAR,bioisosteres,Organisk kemi},
  language     = {eng},
  pages        = {71},
  publisher    = {ARRAY(0xb2ee510)},
  title        = {A mapping of the interactions between a moth sex pheromone component and its receptor},
  year         = {1996},
}