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

dc.contributor.authorLIU, Z. W.
hal.structure.identifierChimie et Biologie des Membranes et des Nanoobjets [CBMN]
dc.contributor.authorHU, Xiaobo
dc.contributor.authorABRAMYAN, A. M.
dc.contributor.authorMESZAROS, A.
dc.contributor.authorCSEKEI, M.
dc.contributor.authorKOTSCHY, A.
hal.structure.identifierChimie et Biologie des Membranes et des Nanoobjets [CBMN]
dc.contributor.authorHUC, Ivan
dc.contributor.authorPOPHRISTIC, V.
dc.date.accessioned2020-07-09T14:16:45Z
dc.date.available2020-07-09T14:16:45Z
dc.date.issued2017-03
dc.identifier.issn0947-6539
dc.identifier.urihttps://oskar-bordeaux.fr/handle/20.500.12278/10294
dc.description.abstractEnMetadynamics 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.
dc.title.enComputational Prediction and Rationalization, and Experimental Validation of Handedness Induction in Helical Aromatic Oligoamide Foldamers
dc.typeArticle de revue
dc.identifier.doi10.1002/chem.201605082
dc.subject.halChimie/Matériaux
bordeaux.journalChemistry-a European Journal
bordeaux.page3605-3615
bordeaux.volume23
bordeaux.hal.laboratoriesInstitut de Chimie & de Biologie des Membranes & des Nano-objets (CBMN) - UMR 5248*
bordeaux.hal.laboratoriesInstitut de Chimie & de Biologie des Membranes & des Nano-objets (CBMN, UMR 5248)
bordeaux.issue15
bordeaux.institutionUniversité de Bordeaux
bordeaux.institutionBordeaux INP
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