We have recently developed a silver-promoted coupling of thioamides and amino acids to generate peptide imides. We have now elaborated this method for native chemical bond formation at asparagine ligation sites. The ligation proceeds via coupling of a peptide C-terminal carboxylate with a peptide containing an N-terminal asparagine thioamide, followed by rapid O-N intramolecular acyl migration to afford a native amide bond.

Silver(I)-promoted asparagine-based peptide ligation employing an <i>N</i>-terminal asparagine thioamide

253rd National Meeting (2017)

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

Silver(I)-promoted asparagine-based peptide ligation employing an N-terminal asparagine thioamide