Synthesis and application of single-isomer 6-mono(alkylimidazolium)-β-cyclodextrins as chiral selectors in chiral capillary electrophoresis

Abstract

Novel single isomers of positively charged β-CDs were prepared via nucleophilic substitution of 6-monotosyl-β-CD with alkylimidazoles to afford 6-mono(alkylimidazolium)-β-CD tosylates and then 6-mono(alkylimidazolium)-β-CD chlorides by anion exchange. The chiral resolution abilities of these cationic CDs were studied by CE using dansyl (Dns)-amino acids as model analytes. From the experimental results, it was found that both resolution and selectivity of these cationic CDs were dependent on the following parameters: concentration of chiral selectors, pH of the running buffer, counteranions of the CDs, side chain length of the n-alkyl-imidazolium cation, temperature of the capillary column, and organic modifier used. The concentration of chiral selectors required for enantioseparation varied from 3 to 30 mM. The BGE pH played an important role in the resolution of Dns-amino acids. For acidic BGEs, chiral resolution increased with pH (4.0-6.0) and reached a local maximum at pH 6.0. However, better resolutions were obtained with basic phosphate buffer at pH 9.6. Methanol was found to be an effective organic modifier for the resolution of Dns-amino acids by CE. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.