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

Ko Urushibara, Yann Ferrand, Zhiwei Liu, Hyuma Masu, Vojislava Pophristic, Aya Tanatani, Ivan Huc

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)7888-7892
Number of pages5
JournalAngewandte Chemie - International Edition
Volume57
Issue number26
DOIs
StatePublished - Jun 25 2018
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • General Chemistry

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