« Previous Abstract"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"    Next AbstractFate of Ah receptor agonists during biological treatment of an industrial sludge containing explosives and pharmaceutical residues »

Bioorg Med Chem

Title:		Enantiomers of cis- and trans-3-(4-propyl-cyclopent-2-enyl) propyl acetate. A study on the bioactive conformation and chiral recognition of a moth sex pheromone component
Author(s):		Gustavsson AL; Larsson MC; Hansson BS; Liljefors T;
Address:		"Center for Chemistry and Chemical Engineering, Lund University, Sweden"
Journal Title:		Bioorg Med Chem
Year:		1997
Volume:		5
Issue:		12
Page Number:		2173 - 2183
DOI:		10.1016/s0968-0896(97)00162-4
ISSN/ISBN:		0968-0896 (Print) 0968-0896 (Linking)
Abstract:		"The enantiomers of cis- and trans-3-(4-propyl-cyclopent-2-enyl) propyl acetate, which are conformationally constrained analogues of (Z)-5-decenyl acetate (1), a sex pheromone component of the turnip moth, Agrotis segetum, have been synthesized and tested using the electrophysiological single-sensillum technique. The analogues mimic a cisoid and transoid conformation of 1, respectively. In addition, the enantiomers of each of the cis- and trans-isomers are conformationally constrained analogues of enantiomeric cisoid and transoid conformations of 1. Thus, the compounds prepared and tested are well suited to investigate the nature of the bioactive conformation of the natural pheromone component 1 and the chiral sense of its interaction with the receptor. Electrophysiological single-sensillum recordings show that the activity of the most active cis-isomer, which has a (1S,4R)-configuration, is more than two orders of magnitude higher than that of the most active trans-isomer. Furthermore, the (1S,4R)-isomer is at least 100 times more active than its enantiomer. These results strongly support a previously proposed cisoid bioactive conformation of 1. Furthermore, the (1S,4R)-configuration of most active stereoisomer identifies the chiral sense of the interaction between the natural pheromone component 1 and its receptor"
Keywords:		"Acetates/*chemistry/pharmacology Animals Electrophysiology Isomerism Male Models, Chemical Models, Molecular Moths Sense Organs/drug effects/physiology Sex Attractants/*chemistry/pharmacology;"
Notes:		"MedlineGustavsson, A L Larsson, M C Hansson, B S Liljefors, T eng Research Support, Non-U.S. Gov't England 1998/02/12 Bioorg Med Chem. 1997 Dec; 5(12):2173-83. doi: 10.1016/s0968-0896(97)00162-4"