Subsequent copper-catalyzed azide-alkyne cycloaddition allows for a chemoselective and mild functionalization of peptides with azide-bearing ligation partners. One possible application is the glycosylation of peptides, including the fast incorporation of short-lived ¹⁸F-labelled carbohydrates.

Reaction between an S-propargyl-cysteine bearing peptide and an azido-functionalized D-galactose.

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References:

• ‘Click’ glycosylation of peptides through cysteine propargylation and CuAAC; S. Lamandé-Langle, C. Collet, R. Hensienne, C. Vala, F. Chrétien, Y. Chapleur, A. Mohamadi, P. Lacolley and V. Regnault; Bioorganic & Medicinal Chemistry 2014; 22: 6672-6683. doi:https://doi.org/10.1016/j.bmc.2014.09.056
• Neoglycopeptides through direct functionalization of cysteine; C. Vala, F. Chrétien, E. Balentova, S. Lamandé-Langle and Y. Chapleur; Tetrahedron letters 2011; 52: 17-20. doi:https://doi.org/10.1016/j.tetlet.2010.10.021
• Photoinduced Addition of Glycosyl Thiols to Alkynyl Peptides: Use of Free-Radical Thiol−Yne Coupling for Post-Translational Double-Glycosylation of Peptides; M. Lo Conte, S. Pacifico, A. Chambery, A. Marra and A. Dondoni; The Journal of Organic Chemistry 2010; 75: 4644-4647. doi:10.1021/jo1008178
• On the Function and Structure of Synthetically Modified Porins; S. Reitz, M. Cebi, P. Reiß, G. Studnik, U. Linne, U. Koert and L.-O. Essen; Angewandte Chemie International Edition 2009; 48: 4853-4857. doi:10.1002/anie.200900457
• Non-enzymatic Covalent Protein Labeling Using a Reactive Tag; H. Nonaka, S. Tsukiji, A. Ojida and I. Hamachi; Journal of the American Chemical Society 2007; 129: 15777-15779. doi:10.1021/ja074176d