Synthesis of anion binding capsules intended for aqueous solutions using olefin metathesis

CHED 333

Kevin M. Yehl, yehlk@mailbox.sc.edu1, Thomas Fiehn2, and Stefan Kubik2. (1) Department of Chemistry and Biochemistry, University of South Carolina, 631 Sumter St., Columbia, SC 29033, (2) Faculty of Chemistry, Technical University of Kaiserslautern, Kaiserslautern, 67663, Germany
Formation of cage-like molecules capable of binding anions in competitive aqueous solvents has been difficult for chemists. Recently it has been discovered through synthesis of cyclic hexapeptide 1 derived from alternating L-proline and 6-aminopicolinic acid subunits that good affinity for anions such as sulfate and iodide in water/methanol mixtures can be achieved through a sandwich-like 2:1 complex. Improved anion affinity can be attained through the addition of a proper linkage between these molecules of 1 receptors. These findings have led to the development of a new class of cage-like capsules capable of encapsulating anions in competitive aqueous solvents through the synthesis of cyclopeptide composed of three substituents with terminal double bonds 2. Olefin metathesis is used to synthesize these cage-like target receptors. The potential for enhanced anion affinity of the receptors will be investigated by NMR of the exclusive cyclopeptide with the complex, and by MS (ESI and MALDI).

 

Undergraduate Research Poster Session
2:30 PM-4:30 PM, Monday, August 20, 2007 BCEC -- Exhibit Hall - B2, Poster

Division of Chemical Education

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007