Despite advances in solid phase peptide synthesis and peptide ligation, challenges remain in the assembly of polypeptides through coupling of peptide fragments. Herein we describe a new method for peptide fragment coupling employing the Ag(I)-promoted transformation of peptide thioamides. This process proceeds an isoimide-tethered intermediate, which undergoes an O-N acyl transfer to generate the polypeptide. This method is applicable to both solution- and solid-phase coupling.
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