Metathesis assisted synthesis of cyclic peptides

摘要

Installation of reversible, metathesis-active tethers into linear peptide sequences can be used to promote formation of cyclic peptide amides and esters.rnHead to tail cyclised peptides are unusual but not uncommon in nature, and have been isolated from marine organisms, bacteria and plants. There is a growing interest in cyclic analogues of naturally occurring and synthetic linear peptides. Simple cyclisation of the protein backbone can offer greater resistance to proteolytic degradation and hence an improved pharmacokinetic profile.3 Nature facilitates cyclisation via a variety of covalent interactions between side chain functionalities, including cystine, dityrosine, ester and lactam linkages, and ligation of the N- and C-termini.