Christiane Funk / Chemistry & Biochemistry / Faculty Mentor: Frank Foss
The Asian corn borer (Ostrinia furnacalis) is a species of moth that is responsible for significant crop damage across Asia and the Pacific Islands, specifically targeting staple crops such as corn, cotton, millet, and hops, resulting in annual yield losses estimated at 6-9 million tons. The perpetuation of this species relies on a pheromone binding protein (PBP2) present in male antennae which binds to the female sex pheromone (E/Z)-12-tetradecenyl acetate. After binding to the pheromone, PBP2 transports it from the antennae to the olfactory receptor neuron where the pheromone is released, prompting the male response. PBP2 is highly sensitive and allows male moths to find mating partners across large distances, and though the structure of the protein has been studied and characterized by both NMR and circular dichroism, the binding and release mechanisms require further investigation. Our aim is to synthesize (E/Z)-12-tetradecenyl acetate and biomimetic derivatives thereof to probe and potentially inhibit PBP2’s signaling pathway to impede mating. These target molecules were designed with three key components: a metabolically stable ester isostere headgroup, “U-shaped” central configuration, and an unsaturated lipophilic tail. Selection of targets was done through computer-aided docking.
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