Bioisosteric Approach to Elucidation of Binding of the Acetate Group of a Moth Sex Pheromone Component to Its Receptor：（醋酸Bioisosteric绑定的方法说明群蛾性信息素成分的受体）.pdfVIP

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Bioisosteric Approach to Elucidation of Binding of the Acetate Group of a Moth Sex Pheromone Component to Its Receptor：（醋酸Bioisosteric绑定的方法说明群蛾性信息素成分的受体）.pdf

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Journal of Chemical Ecology, Vol. 23, No. 12, 1997 BIOISOSTERIC APPROACH TO ELUCIDATION OF BINDING OF THE ACETATE GROUP OF A MOTH SEX PHEROMONE COMPONENT TO ITS RECEPTOR ANNA-LENA GUSTAVSSON,1 MALENA TUVESSON, 1,4 MATTIAS C. LARSSON,2 WU WENQI,2 BILL S. HANSSON,2 and TOMMY LILJEFORS3,* 1Organic Chemistry 1 Center for Chemistry and Chemical Engineering, Lund University P. O. Box 124, S-221 00 Lund, Sweden 2Department of Ecology, Lund University S-223 62 Lund, Sweden 3Department of Medicinal Chemistry, The Royal Danish School of Pharmacy DK-2100 Copenhagen, Denmark (Received January 31, 1997; accepted August 3, 1997) Abstract–A number of analogs of (Z)-5-decenyl acetate, a pheromone com- ponent of the turnip moth, Agrotis segetum, in which the acetate group has been replaced by functional groups that may function as bioisosters, have been synthesized and tested using single-cell electrophysiology.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 activities have been interpreted in terms of the molecular electrostatic potentials of the polar functional group as calculated by ab initio quantum mechanical calcu- lations. It is concluded that both oxygens of the acetate group in (Z)-S-decenyl acetate contribute to the interactions between the pheromone component and its receptor. Furthermore