Thioamide substitution in the peptide backbone has several applications in studying proteolysis, including as protease probes and selective protease inhibitors. To date, we have used model substrates to investigate the positional effects these thioamide substitutions have on proteolysis rates, as well examining the ability of thioamides to stabilize peptides for imaging applications. In order to determine the positional effects of thioamides, we have examined several model peptides with a thioamide scanned from the P3 position to the P3' position and identified thioamide perturbing and non-perturbing positions.  Further mechanistic investigation showed that the primary effect of the thioamide is often to prevent binding to the protease. Finally, incorporation of a thioamide into a peptide scaffold that is known to selectively bind the neuropeptide Y Y1 receptor showed increase serum stability, while retaining affinity for the receptor. These studies show that thioamides can be used to create stabilized imaging peptides and are helping to guide our understanding of where is best to place thioamides to obtain the desired effects.  <br/>

Positional effects of thioamides on serine protease activity: Mechanistic studies and application to stabilize cancer imaging peptides

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.