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Impact of C α ‐Chirality on Supramolecular Self‐Assembly in Cyclo‐2:1‐[α/aza]‐Hexamers ( d / l ‐Phe‐azaPhe‐Ala) 2
Author(s) -
Ibrahim Mohamed Ibrahim Abdelmoneim,
Zhou Zhou,
Deng Cheng,
Didierjean Claude,
Vanderesse Régis,
Bodiguel Jacques,
AverlantPetit MarieChristine,
JamartGrégoire Brigitte
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700555
Subject(s) - supramolecular chemistry , stacking , intramolecular force , hydrogen bond , intermolecular force , chemistry , monomer , chirality (physics) , crystallography , supramolecular assembly , covalent bond , self assembly , stereochemistry , nuclear magnetic resonance spectroscopy , supramolecular chirality , molecule , crystal structure , organic chemistry , polymer , nambu–jona lasinio model , chiral symmetry breaking , physics , quantum mechanics , quark
The design of new cyclic pseudopeptides of the sequence 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 studies showed the ability of this series to adopt β‐turn conformation in solid state, whereas in solution an 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 increases in concentration that favor the supramolecular construction in which the macrocyles are stacking over each other and stabilized by several non‐covalent intermolecular interactions.