One‐Pot Ligation–Oxidative Deselenization at Selenocysteine and Selenocystine

Abstract

The use of native chemical ligation at selenocysteine (Sec) residues with peptide thioesters and additive‐free selenocystine ligation with peptides bearing phenyl selenoesters, in concert with one‐pot oxidative deselenization chemistry, is described. These approaches provide a simple and rapid method for accessing native peptides with serine in place of Sec at the ligation junction. The efficiency of both variants of the one‐pot ligation–oxidative deselenization chemistry is probed through the synthesis of a MUC5AC‐derived glycopeptide.