In recent years a range of novel amide ligation strategies have been developed, many incorporating sulfur-containing reagents as carboxylic acid surrogates.<sup> </sup>We have recently developed a novel method for peptide synthesis based on the reaction of thioamides with carboxylic acids in the presence of silver(I) to generate imides, followed by selective imide cleavage.<br/>Recent progress in this area will be highlighted, including investigations of the reaction mechanism and domino acyl-transfer processes for self-immolative imide cleavage and site-specific amino acid insertion.<br/>A novel peptide ligation strategy will be decribed in which peptides containing an N-terminal asparagine thioamide are linked to peptides with a free C-terminal acid.

Acyl transfer reactions in peptide synthesis and ligation

253rd National Meeting (2017)

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