Date of Award
Spring 2014
Degree Name
Bachelor of Science
Major
Biochemistry
First Advisor
Timothy Curran
Abstract
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.
Recommended Citation
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, https://digitalrepository.trincoll.edu/theses/423
Included in
Amino Acids, Peptides, and Proteins Commons, Enzymes and Coenzymes Commons, Inorganic Chemicals Commons, Organic Chemicals Commons
Comments
Senior thesis completed at Trinity College for the degree of Bachelor of Science in Biochemistry.