“…[13][14][15][16][17] Our choice to incorporate triazoles [12] derived from the extensive use of this heteroaromatic unit into peptide and peptoids field: [18] in fact, since the first publication by Ghadiri and coworkers, [19] this moiety, as bioisostere of amide bond, has been introduced for head-to-tail macrocyclization, side chain to-side chain connection and conjugation of ligands to the peptidomimetic skeleton. [20][21][22][23][24] The presence of the intriguing 1,2,3-triazole moiety in the oligoamide backbone further rigidifies the macrocyclic structures, amplifying, at the same time, the biomimicry potentials, thanks to its known abilities to establish hydrogen and halogen bonding and metal coordination. [25,26] With the idea to design novel nitrogen-containing macrocycles and better understand the effect of chiral side chains on the overall morphology and conformational attitudes [27] of triazolopeptoids, herein we report the synthesis of triazolopeptoid 4 and 5 containing properly arranged N-(S)-(1phenylethyl)glycine (Nspe) and benzyl side chains.…”