Peptoids as a Chiral Stationary Phase for Liquid Chromatography: Insights from Molecular Dynamics Simulations
| Autor: | Otello Maria Roscioni, Corentin Tonneaux, Sébastien Hoyas, Pascal Gerbaux, Luca Muccioli, Jérôme Cornil |
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| Přispěvatelé: | Hoyas S., Roscioni O.M., Tonneaux C., Gerbaux P., Cornil J., Muccioli L. |
| Rok vydání: | 2021 |
| Předmět: |
Polymers and Plastics
Molecular Conformation Bioengineering Stereoisomerism 02 engineering and technology Molecular Dynamics Simulation 010402 general chemistry 01 natural sciences Biomaterials Peptoids Molecular dynamics Materials Chemistry Structural isomer Side chain Chromatography High Pressure Liquid Chromatography Hydrogen bond Chemistry Elution 021001 nanoscience & nanotechnology 0104 chemical sciences Racemic mixture Enantiomer 0210 nano-technology Chromatography Liquid |
| Zdroj: | Biomacromolecules. 22:2573-2581 |
| ISSN: | 1526-4602 1525-7797 |
| Popis: | 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 (Nspe) 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 Nspe 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. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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