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Evaluation of the chiral separation ability of single‐isomer cationic β‐cyclodextrins in capillary electrophoresis
Author(s) -
Wang Yiying,
Zhou Jie,
Liu Yun,
Tang Jian,
Tang Weihua
Publication year - 2014
Publication title -
electrophoresis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.666
H-Index - 158
eISSN - 1522-2683
pISSN - 0173-0835
DOI - 10.1002/elps.201400198
Subject(s) - chemistry , capillary electrophoresis , cyclodextrin , cationic polymerization , aqueous solution , hydrogen bond , alkyl , molecule , solubility , ammonium chloride , chiral derivatizing agent , hydrophobic effect , chromatography , enantiomer , combinatorial chemistry , organic chemistry , chiral column chromatography
Eight single‐isomer ammonium‐β‐cyclodextrin derivatives with different side chains were successfully developed as chiral selectors for the chiral separation of selected racemates in capillary electrophoresis. The number of substituted groups at N‐atom as well as the alkyl chain length greatly influenced the chiral separation. With the numbers of hydroxylalkyl groups at N‐atom growing, the aqueous solubility of resolving agents were distinctly decreased and chiral separation ability was also significantly reduced. The apparent complex stability constants between CD s and analytes were further determined. The best enantioseparations of hydroxyl acids was achieved with the use of mono‐6 A ‐(3‐hydroxypropyl)‐1‐ammonium‐β‐cyclodextrin chloride and mono‐6 A ‐(3‐methoxypropyl)‐1‐ammonium‐β‐cyclodextrin chloride. The nuclear magnetic resonance experiments were carried out using them with mandelic acid as guest molecules, revealing the inclusion pattern as well as electrostatic interactions and hydrogen bonding interactions as additional chiral driving force. The contribution of potential interaction sites in the sidearm could enhance the enantioseparations.