Frustrated Helicity: Joining the Diverging Ends of a Stable Aromatic Amide Helix to Form a Fluxional Macrocycle - CNRS - Centre national de la recherche scientifique Accéder directement au contenu
Article Dans Une Revue Angewandte Chemie Année : 2018

Frustrated Helicity: Joining the Diverging Ends of a Stable Aromatic Amide Helix to Form a Fluxional Macrocycle

Zhiwei Liu
Hyuma Masu
  • Fonction : Auteur
Vojislava Pophristic
  • Fonction : Auteur
Aya Tanatani
  • Fonction : Auteur

Résumé

Macrocyclization of a stable two-turn helical aromatic pentamide, that is, an object with diverging ends that are not prone to cyclization, was made possible by the transient introduction of disruptors of helicity in the form of acid-labile dimethoxybenzyl tertiary amide substituents. After removal of the helicity disruptors, NMR, X-ray crystallography, and computational studies show that the macrocycle possesses a strained structure that tries to gain as high a helical content as possible despite being cyclic. Two points of disruption of helicity remain, in particular a cis amide bond. This point of disruption of helicity can propagate along the cycle in a fluxional manner according to defined trajectories to produce ten degenerate conformations.

Domaines

Matériaux

Dates et versions

hal-02536947 , version 1 (08-04-2020)

Identifiants

Citer

Ko Urushibara, Yann Ferrand, Zhiwei Liu, Hyuma Masu, Vojislava Pophristic, et al.. Frustrated Helicity: Joining the Diverging Ends of a Stable Aromatic Amide Helix to Form a Fluxional Macrocycle. Angewandte Chemie, In press, 57 (26), pp.7888-7892. ⟨10.1002/anie.201802159⟩. ⟨hal-02536947⟩

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