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The study of enantioselectivity of all regioisomers of mono‐carboxymethyl‐β‐cyclodextrin used as chiral selectors in CE
Author(s) -
Navrátilová Klára,
Řezanka Pavel,
Řezanka Michal,
Sýkora David,
Jindřich Jindřich,
Král Vladimír
Publication year - 2013
Publication title -
journal of separation science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.72
H-Index - 102
eISSN - 1615-9314
pISSN - 1615-9306
DOI - 10.1002/jssc.201201144
Subject(s) - cyclodextrin , structural isomer , chemistry , chromatography , combinatorial chemistry , stereochemistry
This work documents the influence of the position of single carboxymethyl group on the β‐cyclodextrin skeleton on the enantioselectivity. These synthesized monosubstituted carboxymethyl cyclodextrin ( CD ) derivatives, native β‐cyclodextrin, and commercially available carboxymethyl‐β‐cyclodextrin with degree of substitution approximately 3 were used as additives into the BGE consisting of phosphate buffer at 20 mmol/L concentration, pH 2.5, and several biologically significant low‐molecular‐mass chiral compounds were enantioseparated by CE . The results indicate that different substituent location on β‐cyclodextrin skeleton has a significant influence on the enantioseparation of the investigated enantiomers. The enantioselectivity of 2 I ‐ O ‐regioisomer was better than with native β‐cyclodextrin. Comparable results to native β‐cyclodextrin were obtained for 6 I ‐ O ‐ regioisomer and the enantioselectivity of 3 I ‐ O ‐regioisomer was even worse than with native β‐cyclodextrin. Commercially available derivative of CD provides better resolutions than the monosubstituted carboxymethyl CD derivatives for most of the investigated analytes.