BIOISOSTERIC APPROACH TO ELUCIDATION OF BINDING OF THE ACETATE GROUP OF A MOTH SEX-PHEROMONE COMPONENT TO ITS RECEPTOR

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of (Z)-5-decenyl acetate, a pheromone component of the turnip moth, Agrotis segetum, in which the acetate group has been replaced by functional groups that may function as bioisosters, have been synthesized and tested using single-cell electrophysiology.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 a ctivities have been interpreted in terms of the molecular electrostati c potentials of the polar functional group as calculated by ab initio quantum mechanical calculations. It is concluded that both oxygens of the acetate group in (Z)-5-decenyl acetate contribute to the interacti ons between the pheromone component and its receptor. Furthermore, the results indicate that the crucial interaction between the carbonyl gr oup and the receptor, which is most probably a hydrogen bonding intera ction, takes place in a direction pointing away from the hydrocarbon c hain of the pheromone component.