Metal-free, regioselective triazole ligations that deliver locked cis peptide mimetics

Ahsanullah; P. Schmieder; R. Kühne; J. Rademann

Angew. Chem. Int. Ed. 48, 5042-5045 (2009)

Metal-free triazole turns: 1,5-Disubstituted peptidyl triazoles are obtained regioselectively from the 1,3-dipolar cycloaddition of peptidyl phosphoranes and azides. Peptide turns are thus formed that contain a conformationally locked cis peptide bond. Being regioselective and free of heavy metals, this reaction may find broad application in chemical biology and medicinal chemistry.