Propargylamine Amino Acids as Constrained Nε-Substituted Lysine Mimetics

Herein,\nalkylated propargylamines are reported as constrained lysine\nmimetics and constructed in a single step using a copper(I)-catalyzed\nA<sup>3</sup>-coupling reaction. Using multiple secondary amines,\nthe reaction allowed the generation of a structurally diverse set\nof <i>N</i>-Fmoc protected amino acid derivatives. In addition,\nthe A<sup>3</sup>-reaction was applied on solid phase via the assembly\nof short model tripeptides. Moreover, the internal alkyne moiety allowed\nfurther functionalization toward novel 1,4,5-trisubstituted 1,2,3-triazole-based\namino acids.