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Elucidation of the Enantiodiscrimination Properties of a Nonracemic Chiral Alignment Medium through Gel‐based Capillary Electrochromatography: Separation of the Mefloquine Stereoisomers

Enantiodiscrimination and enantioseparation are two highly important processes in chemistry, often performed by using NMR spectroscopy and chromatography. For a better understanding of the mechanistic details, the same system should be studied by both methods. In addition, isotropic and anisotropic...

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Autores principales: Al‐Massaedh, “Ayat Allah”, Schmidt, Manuel, Pyell, Ute, Reinscheid, Uwe M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5062011/
https://www.ncbi.nlm.nih.gov/pubmed/27777838
http://dx.doi.org/10.1002/open.201600085
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author Al‐Massaedh, “Ayat Allah”
Schmidt, Manuel
Pyell, Ute
Reinscheid, Uwe M.
author_facet Al‐Massaedh, “Ayat Allah”
Schmidt, Manuel
Pyell, Ute
Reinscheid, Uwe M.
author_sort Al‐Massaedh, “Ayat Allah”
collection PubMed
description Enantiodiscrimination and enantioseparation are two highly important processes in chemistry, often performed by using NMR spectroscopy and chromatography. For a better understanding of the mechanistic details, the same system should be studied by both methods. In addition, isotropic and anisotropic NMR parameters should be obtained, the latter using alignment media so that residual dipolar couplings and chemical‐shift anisotropies can be measured. Consequently, a chiral alignment medium was used for the first time in chiral gel‐based capillary electrochromatography with the four stereoisomers of the antimalaria drug mefloquine as test compounds. Chromatographic data verify that enantiodiscrimination obtained with this alignment gel is caused by differences in the equilibrium constants related to associate formation. Hence, the chromatographic separation provides physicochemical data that form a basis for the understanding and optimization of alignment processes, and vice versa.
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spelling pubmed-50620112016-10-24 Elucidation of the Enantiodiscrimination Properties of a Nonracemic Chiral Alignment Medium through Gel‐based Capillary Electrochromatography: Separation of the Mefloquine Stereoisomers Al‐Massaedh, “Ayat Allah” Schmidt, Manuel Pyell, Ute Reinscheid, Uwe M. ChemistryOpen Full Papers Enantiodiscrimination and enantioseparation are two highly important processes in chemistry, often performed by using NMR spectroscopy and chromatography. For a better understanding of the mechanistic details, the same system should be studied by both methods. In addition, isotropic and anisotropic NMR parameters should be obtained, the latter using alignment media so that residual dipolar couplings and chemical‐shift anisotropies can be measured. Consequently, a chiral alignment medium was used for the first time in chiral gel‐based capillary electrochromatography with the four stereoisomers of the antimalaria drug mefloquine as test compounds. Chromatographic data verify that enantiodiscrimination obtained with this alignment gel is caused by differences in the equilibrium constants related to associate formation. Hence, the chromatographic separation provides physicochemical data that form a basis for the understanding and optimization of alignment processes, and vice versa. John Wiley and Sons Inc. 2016-09-16 /pmc/articles/PMC5062011/ /pubmed/27777838 http://dx.doi.org/10.1002/open.201600085 Text en © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial‐NoDerivs (http://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Full Papers
Al‐Massaedh, “Ayat Allah”
Schmidt, Manuel
Pyell, Ute
Reinscheid, Uwe M.
Elucidation of the Enantiodiscrimination Properties of a Nonracemic Chiral Alignment Medium through Gel‐based Capillary Electrochromatography: Separation of the Mefloquine Stereoisomers
title Elucidation of the Enantiodiscrimination Properties of a Nonracemic Chiral Alignment Medium through Gel‐based Capillary Electrochromatography: Separation of the Mefloquine Stereoisomers
title_full Elucidation of the Enantiodiscrimination Properties of a Nonracemic Chiral Alignment Medium through Gel‐based Capillary Electrochromatography: Separation of the Mefloquine Stereoisomers
title_fullStr Elucidation of the Enantiodiscrimination Properties of a Nonracemic Chiral Alignment Medium through Gel‐based Capillary Electrochromatography: Separation of the Mefloquine Stereoisomers
title_full_unstemmed Elucidation of the Enantiodiscrimination Properties of a Nonracemic Chiral Alignment Medium through Gel‐based Capillary Electrochromatography: Separation of the Mefloquine Stereoisomers
title_short Elucidation of the Enantiodiscrimination Properties of a Nonracemic Chiral Alignment Medium through Gel‐based Capillary Electrochromatography: Separation of the Mefloquine Stereoisomers
title_sort elucidation of the enantiodiscrimination properties of a nonracemic chiral alignment medium through gel‐based capillary electrochromatography: separation of the mefloquine stereoisomers
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5062011/
https://www.ncbi.nlm.nih.gov/pubmed/27777838
http://dx.doi.org/10.1002/open.201600085
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