1. Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, MI 48202 (USA);2. Centre de Recherche CNRS de Gif‐sur‐Yvette, Institut de Chimie des Substances Naturelles, Avenue de la Terrasse, 91198 Gif‐sur‐Yvette (France), Fax: (+33)?1‐6907‐7752
Abstract:
Highly activated thioesters formed by the rapid reaction of C‐terminal thioacids derived from protected amino acids and peptides with the Sanger reagent and other electron‐deficient aryl halides in the presence of a free amine immediately form a peptide bond with the amine. This essentially epimerization‐free method was used for the 4+4 block synthesis of a hindered octapeptide (see scheme; Boc, Pbf, and Trt are protecting groups).
