Impact of Cα‐Chirality on Supramolecular Self‐Assembly in Cyclo‐2:1‐[α/aza]‐Hexamers (d/l‐Phe‐azaPhe‐Ala)2
Résumé
The design of new cyclic pseudopeptides of the se- quence 2:1-[α/aza]-hexamers, which contain aza-amino acid motifs, has gained much prominence to be involved in several potential applications. X-ray, FTIR, and NMR spectroscopy stud- ies showed the ability of this series to adopt -turn conforma- tion in solid state, whereas in solution an equilibrium between the monomeric states (stabilized by -turns through intra- molecular 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 increases in concentration that favor the supramolecular construction in which the macro- cyles are stacking over each other and stabilized by several non-covalent intermolecular interactions.