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

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.