Computational prediction and rationalization, and experimental validation of handedness induction in helical aromatic oligoamide foldamers

Zhiwei Liu, Xiaobo Hu, Ara M. Abramyan, Mészáos, Márton Csékei, András Kotschy, Ivan Huc, Vojislava Pophristic

Research output: Contribution to journalArticlepeer-review

20 Scopus citations

Abstract

Metadynamics simulations were used to describe the conformational energy landscapes of several helically folded aromatic quinoline carboxamide oligomers bearing a single chiral group at either the C or N terminus. The calculations allowed the prediction of whether a helix handedness bias occurs under the influence of the chiral group and gave insight into the interactions (sterics, electrostatics, hydrogen bonds) responsible for a particular helix sense preference. In the case of camphanyl-based and morpholine-based chiral groups, experimental data confirming the validity of the calculations were already available. New chiral groups with a proline residue were also investigated and were predicted to induce handedness. This prediction was verified experimentally through the synthesis of proline-containing monomers, their incorporation into an oligoamide sequence by solid phase synthesis and the investigation of handedness induction by NMR spectroscopy and circular dichroism.

Original languageEnglish (US)
Pages (from-to)3605-3615
Number of pages11
JournalChemistry - A European Journal
Volume23
Issue number15
DOIs
StatePublished - Mar 13 2017
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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