Studies towards small-molecule-receptors selective for phospholipid anionic head groups in bacterial membranes
Meece, Frederick A.
AdvisorBurns, Dennis H.
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Receptors specific for inorganic anions have been described for several decades. Several of these anions, i.e. chloride, phosphate, and acetate are essential in biology. A novel neutral anion receptor specific for the phosphate containing head group of bacterial membrane fatty acids was conceptualized as part of a possible broad spectrum antibiotic. The receptor and several related derivatives were synthesized over fourteen steps. The most important step which involved placing ureidomethylene groups to a bis‐phenolic scaffold was developed as a novel method. The method was probed for scope and utility with a variety of aromatic nucleophiles. The aforementioned anion receptors were tested for binding capabilities against several inorganic anions, and against a synthetic tetrabutylammonium salt of a phospholipid. Several of the derivatives were also tested for antibiotic activity against several species of gram negative bacteria. Finally, the receptors were used to bind chloride anion in solvents containing a variable amount of water to determine if the presence of water would result in stronger anion binding.
Thesis (Ph.d.)--Wichita State University, College of Liberal Arts and Sciences, Dept. of Chemistry