Exploiting thioamides in the synthesis and functionalisation of peptides

Title: Exploiting thioamides in the synthesis and functionalisation of peptides

Speaker: Professor Craig Hutton from the University of Melbourne 

Abstract: New methods for peptide synthesis and functionalisation – based on the incorporation of backbone thioamide and amidoxime groups as amide bond replacements – will be presented. The reaction of peptide thioamides in the presence of silver(I) will be highlighted: these reactions involve the initial generation of isoimide intermediates, which can undergo acyl transfer to facilitate a range of functionalisation processes including peptide macrocyclization, ring expansion and glycosylation. Recent progress on the late-stage C–H functionalization of peptides will also be presented. While C–H functionalization of amino acids employing installed ‘directing groups’ has been developed as a valuable method for preparation of non-natural amino acids, elaboration to peptides and proteins is limited by poor selectivity in molecules containing multiple amide groups. Incorporation of an amidoxime as a backbone amide replacement facilitates the site-selective (and ultimately traceless) C–H functionalisation of peptide side chains.

Bio: Craig Hutton completed his PhD at the University of Adelaide followed by postdoctoral studies at the UC Berkeley. He started his independent career at The University of Sydney before moving to The University of Melbourne where he is a Professor in the School of Chemistry. His research interests include the development of novel synthetic methods for the assembly and functionalization of peptides, the synthesis of biologically active cyclic peptide natural products, and the development of radiolabelled peptides for cancer imaging.