Synthesis of Selenium-Alkylated Selenocysteine Derivatives and Their Use in Native Chemical Ligation, Expressed Protein Ligation and the Synthesis of Dehydropeptides
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.
University of Illinois - Urbana-Champaign
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University of Illinois at Urbana-Champaign