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Influence of substituent position and cavity size of the regioisomers of monocarboxymethyl‐α‐, β‐, and γ‐cyclodextrins on the apparent stability constants of their complexes with both enantiomers of Tröger's base
Authors:Pavel Řezanka  Klára Řezanková  Helena Sedláčková  Jindřich Mašek  Lenka Rokosová  Markéta Bláhová  Michal Řezanka  Jindřich Jindřich  David Sýkora  Vladimír Král
Affiliation:1. Department of Analytical Chemistry, University of Chemistry and Technology, Prague, Czech Republic;2. Department of Organic Chemistry, Faculty of Science, Charles University in Prague, Prague 2, Czech Republic;3. Institute for Nanomaterials, Advanced Technologies and Innovation, Technical University of Liberec, Liberec 1, Czech Republic
Abstract:Enantiomers of Tröger's base were separated by capillary electrophoresis using 2IO‐, 3IO‐, and 6IO‐carboxymethyl‐α‐, β‐, and γ‐cyclodextrin and native α‐, β‐, and γ‐cyclodextrin as chiral additives at 0–12 mmol/L for β‐cyclodextrin and its derivatives and 0–50 mmol/L for α‐ and γ‐cyclodextrins and their derivatives in a background electrolyte composed of sodium phosphate buffer at 20 mmol/L concentration and pH 2.5. Apparent stability constants of all cyclodextrin–Tröger's base complexes were calculated based on capillary electrophoresis data. The obtained results showed that the position of the carboxymethyl group as well as the cavity size of the individual cyclodextrin significantly influences the apparent stability constants of cyclodextrin–Tröger's base complexes.
Keywords:Capillary electrophoresis  Chiral separation  Cyclodextrin  Regioisomers  Stability constants
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