Physical Sciences and Mathematics Commons^™

Artificial Peptides Containing Ca,A- Disubstituted Amino Acids: Synthesis, Conformational Studies, And Application As Β-Strand Mimics, Yanwen Fu

LSU Doctoral Dissertations

Short peptides containing C^α,α-dipropylglycine (Dpg) at alternating sequence positions were synthesized and examined for conformational behavior. Peptide assembly was performed using Fmoc-solid-phase chemistry where the coupling with PyAOP could be significantly enhanced at elevated temperature. Circular dichroism (CD) and NMR conformational studies revealed that incorporation of Dpg residues induced folded structures into peptides. It was observed that Dpg residues adopted helical conformation in a helix-promoting sequence. The resulting helical structure was comprised of consecutive β-turns whose structure was stabilized by salt bridge in aqueous solution. In this study, the preparation of sterically and polyfunctional C^α,α-disubstituted amino …