An efficient approach for monosulfide bridge formation in solid-phase peptide synthesis

Abstract

An efficient approach for the synthesis of cyclic peptides containing unnatural thioether side-chain bridges, based on the use of (2S)-9-fluorenylmethyl-2-[(tert-butoxycarbonyl)amino]-4-iodobutanoate and its homologue 5-iodopentanoate, derived from Boc-l-Asp-OFm and Boc-l-Glu-OFm, respectively, is reported. The synthesis was performed by a tandem combination of solid-phase peptide synthesis and microwave-assisted cyclization strategy.