Accessing Improbable Foldamer Shapes with Strained Macrocycles

Ko Urushibara, Yann Ferrand, Zhiwei Liu, Kosuke Katagiri, Masatoshi Kawahata, Estelle Morvan, Ryan D'Elia, Vojislava Pophristic, Aya Tanatani, Ivan Huc

Research output: Contribution to journalArticlepeer-review

5 Scopus citations


The alkylation of some secondary amide functions with a dimethoxybenzyl (DMB) group in oligomers of 8-amino-2-quinolinecarboxylic acid destabilizes the otherwise favored helical conformations, and allows for cyclization to take place. A cyclic hexamer and a cyclic heptamer were produced in this manner. After DMB removal, X-ray crystallography and NMR show that the macrocycles adopt strained conformations that would be improbable in noncyclic species. The high helix folding propensity of the main chain is partly expressed in these conformations, but it remains frustrated by macrocyclization. Despite being homomeric, the macrocycles possess inequivalent monomer units. Experimental and computational studies highlight specific fluxional pathways within these structures. Extensive simulated annealing molecular dynamics allow for the prediction of the conformations for larger macrocycles with up to sixteen monomers.

Original languageEnglish (US)
Pages (from-to)11205-11215
Number of pages11
JournalChemistry - A European Journal
Issue number43
StatePublished - Aug 2 2021
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry


Dive into the research topics of 'Accessing Improbable Foldamer Shapes with Strained Macrocycles'. Together they form a unique fingerprint.

Cite this