Synthesis of Selenium-Alkylated Selenocysteine Derivatives and Their Use in Native Chemical Ligation, Expressed Protein Ligation and the Synthesis of Dehydropeptides

Abstract

Finally, an improved, scalable synthesis of Fmoc-phenylselenocysteine is reported. The amino acid was coupled to a model peptide on the solid phase. It was demonstrated that the selenide could be oxidatively eliminated to give a dehydropeptide while still bound to the solid resin. In addition, the peptide acted as a Michael acceptor for a thiol nucleophile. These solid phase reactions were monitored by magic angle spinning NMR spectroscopy.