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One-Pot Ligation-Oxidative Deselenization at Selenocysteine and Selenocystine
Nicholas J Mitchell1, Sameer S Kulkarni1, Lara R Malins1
1School of Chemistry, The University of Sydney, Sydney, NSW, 2006, Australia.
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.
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