Synthesis of α-Trifluoromethyl-α-hydroxy Acid-Peptide Conjugates via Click Chemistry

Authors: Sokolova, Nadezhda V.; Vorobyeva, Daria V.; Osipov, Sergey N.; Vasilyeva, Tamara P.; Nenajdenko, Valentine G.; Synthesis; (2012); 10.1055/s-0031-1289609

A simple and convenient method for the incorporation of fluorinated α-hydroxy acids into peptides is described. The target conjugates were obtained from α-alkynyl-α-trifluoromethyl-α-hydroxy acids and azido peptides via the copper(I)-catalyzed Huisgen cycloaddition reaction (click chemistry). After straightforward deprotection, the α-trifluoromethyl-α-hydroxy acid containing peptides may find important applications in biochemistry and medicinal chemistry.