N-Acyl Transfer Reactions in Peptide Synthesis
We have developed a new method for peptide synthesis through the Ag(I)-promoted coupling of thioamides with carboxylic acids. This process generates an isoimide, which undergoes and N-acyl transfer to generate an imide. The peptide imide can be hydrolysed to generate a native amide bond, or can undergo subsequent acyl transfer reactions to generate a range of modified peptides. We are investigating applications in peptide ligation, peptide residue excision/insertion, and peptide thioester synthesis.
C. A. Hutton, J. Shang and U. Wille, “Synthesis of Peptides by Silver-Promoted Coupling of Carboxylates and Thioamides: Mechanistic Insight from Computational Studies,” Chem. Eur. J. 2016, 22, 3163–3169.
J. Shang, A. Pourvali, J. R. Cochrane and C. A. Hutton, “Steric and Electronic Effects in the Synthesis and Regioselective Hydrolysis of Unsymmetrical Imides,” Aust. J. Chem. 2015, 68, 1854–1858.
A. Pourvali, J. R. Cochrane, C. A. Hutton, “A new method for peptide synthesis in the N–C direction: amide assembly through silver-promoted reaction of thioamides,” Chem. Commun., 2014, 50, 15963–15966.
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