Synthesis of selenocysteine-containing cyclic peptides <i>via</i> tandem <i>N</i>-to-<i>S</i> acyl migration and intramolecular selenocysteine-mediated native chemical ligation

Abstract

Selenocysteine-containing cyclic 8-mer peptides, which were designed to mimic the plausible catalytic tetrad of glutathione peroxidase, were successfully synthesized in one pot via tandem N-to-S acyl migration of N-alkylcysteine (NAC)-containing selenopeptides and intramolecular selenocysteine-mediated native chemical ligation (Sec-NCL) of the generated thioesters.