Enhancement of the helical content and stability induced in a linear oligopeptide by ani, i+4 intramolecularly double stapled, overlapping, bicyclic [31, 22, 5]-(E)ene motif

Abstract

Two consecutive i, i+4 intramolecular, side chain-to-side chain, macrocyclizations of different type carried out on a preformed, partially helical peptide result in a largely predominant, double stapled, overlapping, bicyclic [31,22,5]-(E)ene motif. A detailed ECD and NMR conformational study revealed a significant enhancement of the original helical content and stability, accompanied by an increase of the α-helix amount over that of the 3(10)-helix.