Computational Prediction and Rationalization, and Experimental Validation of Handedness Induction in Helical Aromatic Oligoamide Foldamers
| Autor: | Ádám Mészáros, András Kotschy, Csékei Márton, Ara M. Abramyan, Zhiwei Liu, Xiaobo Hu, Ivan Huc, Vojislava Pophristic |
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| Rok vydání: | 2017 |
| Předmět: |
Steric effects
Circular dichroism 010405 organic chemistry Chemistry Hydrogen bond Organic Chemistry Metadynamics Nanotechnology General Chemistry Nuclear magnetic resonance spectroscopy 010402 general chemistry 01 natural sciences Catalysis 0104 chemical sciences Crystallography Solid-phase synthesis Helix Alpha helix |
| Zdroj: | Chemistry – A European Journal. 23:3605-3615 |
| ISSN: | 1521-3765 0947-6539 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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