Impact of Cα-Chirality on Supramolecular Self-Assembly in Cycclo-2:1[α/aza]-Hexamers (D/L-Phe-azaPhe Ala)2

The design of new cyclic pseudopeptides of the sequence 2:1-[α/aza]-hexamers containing aza-amino acid motifs has gained much prominence to be involved in several potential applications. X-ray, FT-IR, and NMR studies showed the ability of this series to adopt β-turn conformation in solid state, while in solution; equilibrium between the monomeric states (stabilized by β-turns through intramolecular hydrogen bonds), and supramolecular construction (stabilized by intermolecular hydrogen bonds and π-π stacking) predominates. Furthermore, both homo- and heterochiral 2:1-[α/aza]-cyclohexamers 3 and 4, respectively can self-assemble into organized 3D structures with increasing concentration favoring the supramolecular construction where the macrocyles are stacking over each other and stabilized by several non-covalent intermolecular interactions.

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