LIU, Z. W.; HU, Xiaobo; ABRAMYAN, A. M.; MESZAROS, A.; CSEKEI, M.; KOTSCHY, A.; HUC, Ivan; POPHRISTIC, V.

doi:10.1002/chem.201605082

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LIU, Z. W.

HU, Xiaobo
Chimie et Biologie des Membranes et des Nanoobjets [CBMN]

ABRAMYAN, A. M.

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Chemistry-a European Journal. 2017-03, vol. 23, n° 15, p. 3605-3615

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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 Nterminus. 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.< Leer menos

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Computational Prediction and Rationalization, and Experimental Validation of Handedness Induction in Helical Aromatic Oligoamide Foldamers

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