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Impact of Cα‐Chirality on Supramolecular Self‐Assembly in Cyclo‐2:1‐[α/aza]‐Hexamers (d/l‐Phe‐azaPhe‐Ala)2

Abstract : 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.
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Submitted on : Monday, March 4, 2019 - 6:39:59 PM
Last modification on : Friday, January 7, 2022 - 3:54:47 AM

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Mohamed Ibrahim Abdelmoneim Ibrahim, Zhou Zhou, Cheng Deng, Claude Didierjean, Régis Vanderesse, et al.. Impact of Cα‐Chirality on Supramolecular Self‐Assembly in Cyclo‐2:1‐[α/aza]‐Hexamers (d/l‐Phe‐azaPhe‐Ala)2. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2017, 2017 (32), pp.4703-4712. ⟨10.1002/ejoc.201700555⟩. ⟨hal-02056820⟩

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