Abstract:

Chemical building blocks and models can serve as useful tools and surrogates for mimicking peptides in a biological system. In the following chapters of my thesis, I introduce two noncanonical amino acid building blocks that I have synthesized for incorporation into peptides and evaluate their secondary structure formation or biological activity (chapter 1 and chapter 3). I will also describe the use of chemical models derived from the β-amyloid peptide Aβ to investigate and probe the chiral selectivity in β-sheet assembly in aqueous solution (chapter 2). These three chapters of my thesis represent my passion for organic synthesis and NMR spectroscopy, and are linked by a theme of using building blocks and models to investigate peptide folding, assembly, and activity.