Chiral separation of anionic and neutral compounds using a hepta-substituted cationic beta-cyclodextrin as a chiral selector in capillary electrophoresis.
Enantiomeric separations of six anionic and two neutral racemates were achieved using a fully substituted heptakis(6-hydroxyethylamino-6-deoxy)-beta-cyclodextrin (beta-CD-EA) as a chiral selector. As beta-CD-EA provides a dynamic coating on the capillary wall, reverse-polarity capillary electrophoresis (CE) configuration is applied for separations of anionic and neutral chiral compounds. Chiral separations of various classes of anionic and neutral enantiomers were found to be highly dependent on pH because the degree of protonation of beta-CD-EA can alter the shape of the CD cavity by charge repulsion, altering complexation, aiding selectivity, and leading to better enantiomeric separation. In general, the chiral resolution of anionic enantiomers was enhanced at higher pH. This suggests that carboxylate or phosphate groups on the analyte may interact with the protonated amine groups of cationic CD. The successful enantioseparation was achieved in a pH range of 6.6-7.8 for all six anionic analytes, in the presence of 10 mM beta-CD-EA.
Lee
Doowon
D
Department of Chemistry, Center of BioTechnology and Drug Design, Georgia State University, Atlanta, GA 30303, USA.
Shamsi
Shahab A
SA
D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry; D000838:Anions / Q000302:isolation & purification*; D002412:Cations / Q000737:chemistry; D020374:Chromatography, Micellar Electrokinetic Capillary / Q000379:methods*; D003505:Cyclodextrins / Q000138:chemical synthesis* / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D057927:Hydrophobic and Hydrophilic Interactions; D009930:Organic Chemicals / Q000302:isolation & purification; D012680:Sensitivity and Specificity; D013237:Stereoisomerism; D047392:beta-Cyclodextrins
D000588:Amines; D000838:Anions; D002412:Cations; D003505:Cyclodextrins; D009930:Organic Chemicals; D047392:beta-Cyclodextrins; C031215:betadex