Date of Award
Bachelor of Science
The study of β-sheet mimetics represents an important step in understanding the structural and function of β-sheets. The purpose of this report was to develop a β-sheet mimetic through a diphenylacetylene backbone, coordinate the complex to tungsten and determine the structural and conformational characteristics of the complex. In order to characterize the different compounds ESI-MS, 1HNMR, COSY NMR, NOESY NMR, and ROESY NMR were employed. The diphenylacetylene backbone contained two phenyl substituents with a peptide chain of two amino acids. The β-sheet mimetic 1 was successfully synthesized utilizing peptide coupling reactions and a Sonogashira coupling reaction. Previous research by the Curran group has illustrated the ability of alkynylpeptides and dialkynylpeptides to be constrained to specific conformational arrangements upon coordination to tungsten. Compound 1 was successfully coordinated to tungsten to form 15. It was found that compound 15 maintained a β-sheet conformation and was present as two diastereomers. The thesis will detail the synthetic steps taken to create compound 1 and 15 and the NMR experiments that established the conformational characteristics of the β-sheet mimetic.
Herman, Francis, "The Development of a Synthetic Route for a Disubsitituted Diphenylacetylene and Its Conformational Characteristics upon Coordination to Tungsten: A Prospect for Beta-Sheet Studies". Senior Theses, Trinity College, Hartford, CT 2014.
Trinity College Digital Repository, http://digitalrepository.trincoll.edu/theses/423