| Autor: |
Hoyas S; Laboratory for Chemistry of Novel Materials, Center of Innovation and Research in Materials and Polymers, Research Institute for Science and Engineering of Materials, University of Mons, 23 Place du Parc, Mons 7000, Belgium.; Organic Synthesis & Mass Spectrometry Laboratory, Interdisciplinary Center for Mass Spectrometry (CISMa), Center of Innovation and Research in Materials and Polymers (CIRMAP), University of Mons, 23 Place du Parc, Mons 7000, Belgium., Roscioni OM; Department of Industrial Chemistry ≪ Toso Montanari ≫, University of Bologna, Viale Risorgimento 4, 40136 Bologna, Italy.; MaterialX LTD, Bristol BS2 0XJ, U.K., Tonneaux C; Laboratory for Chemistry of Novel Materials, Center of Innovation and Research in Materials and Polymers, Research Institute for Science and Engineering of Materials, University of Mons, 23 Place du Parc, Mons 7000, Belgium., Gerbaux P; Organic Synthesis & Mass Spectrometry Laboratory, Interdisciplinary Center for Mass Spectrometry (CISMa), Center of Innovation and Research in Materials and Polymers (CIRMAP), University of Mons, 23 Place du Parc, Mons 7000, Belgium., Cornil J; Laboratory for Chemistry of Novel Materials, Center of Innovation and Research in Materials and Polymers, Research Institute for Science and Engineering of Materials, University of Mons, 23 Place du Parc, Mons 7000, Belgium., Muccioli L; Department of Industrial Chemistry ≪ Toso Montanari ≫, University of Bologna, Viale Risorgimento 4, 40136 Bologna, Italy. |
| Abstrakt: |
Peptoids are peptide regioisomers with attractive structural tunability in terms of sequence and three-dimensional arrangement. Peptoids are foreseen to have a great potential for many diverse applications, including their utilization as a chiral stationary phase in chromatography. To achieve chiral recognition, a chiral side chain is required to allow specific interactions with a given enantiomer from a racemic mixture. One of the most studied chiral stationary phases, built with ( S )- N -1-phenylethyl ( N spe) units, was shown to be successful in resolving racemic mixtures of binaphthyl derivatives. However, there is currently no description at the atomic scale of the factors favoring its enantioselectivity. Here, we take advantage of steered molecular dynamics simulations to mimic the elution process at the atomic scale and present evidence that the predominantly right-handed helical conformation of N spe peptoids and their ability to form stronger hydrogen bonds with the ( S ) enantiomer are responsible for the chiral recognition of the popular chiral probe 2,2'-bihydroxy-1,1'-binaphthyl. |
