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

Autor: Ibrahim, Mohamed Ibrahim Abdelmoneim, Zhou, Zhou, Deng, Cheng, Didierjean, Claude, Vanderesse, Régis, Bodiguel, Jacques, Averlant-Petit, Marie-Christine, Jamart-Gregoire, Brigitte
Přispěvatelé: Ecole Nationale Supérieure des Industries Chimiques (ENSIC), Université de Lorraine (UL), Laboratoire de Chimie Physique Macromoléculaire (LCPM), Institut de Chimie du CNRS (INC)-Université de Lorraine (UL)-Centre National de la Recherche Scientifique (CNRS), Cristallographie, Résonance Magnétique et Modélisations (CRM2), Université de Lorraine (UL)-Centre National de la Recherche Scientifique (CNRS)
Jazyk: angličtina
Rok vydání: 2017
Předmět:
Zdroj: European Journal of Organic Chemistry
European Journal of Organic Chemistry, Wiley-VCH Verlag, 2017, 2017 (32), pp.4703-4712. ⟨10.1002/ejoc.201700555⟩
ISSN: 1434-193X
1099-0690
DOI: 10.1002/ejoc.201700555⟩
Popis: International audience; 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.
Databáze: OpenAIRE
Externí odkaz: