Synthesis of charged receptors with a bis phenolic ether scaffold, and studies of their binding to Phosphatidylglycerol, a bacterial membrane component

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Jayasinghe, Wedhigangoda A.P.A.
Burns, Dennis H.

An ongoing project of our research group is to develop synthetic receptors for the head group of Phosphatidylglycerol, a bacterial membrane component. Previous studies with bis phenolic oxygen linked scaffoldings with neutral binding sites showed relatively weak binding to the Phosphatidylglycerol (PG) anion. This study reports a fourteen step synthesis of a receptor molecule with a bis-phenolic oxygen ether linked scaffold, leading to an expansion of the binding pocket. The receptor is multifunctional with ammonia binding units for the phosphate anion portion of PG and two bis hydroxyl groups to bind to the glycerol hydroxyls of PG head group. The receptor's initial characterization by means of 1H NMR binding studies with Phosphatidylglycerol anion has also been reported. It also describes the synthesis of a control receptor molecule, and its binding stoichiometry with Phosphatidylglycerol and phosphate anions.

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Thesis (Ph.D.)--Wichita State University, Fairmount College of Liberal Arts and Sciences, Dept. of Chemistry