Application of sulfated cyclodextrins to chiral separations by capillary zone electrophoresis.
Mixtures of randomly substituted sulfated cyclodextrins (degree of substitution, approximately 7-10) were successfully used as chiral additives for the enantioseparation of 56 compounds of pharmaceutical interest, including anesthetics, antiarrhythmics, antidepressants, anticonvulsants, antihistamines, antihypertensives, antimalarials, relaxants, and bronchodilators. The separations were accomplished at pH 3.8, with the anode at the detector end of the column. Under these conditions, in which electroosmotic flow is directed toward the injection end of the column and the electrophoretic mobility of the negatively charged cyclodextrin is toward the detector, none of the analytes reached the detector in the absence of the sulfated cyclodextrin. Most (40) of the successfully resolved enantiomers contained basic functionality and a stereogenic carbon. However, the versatility of this sulfated cyclodextrin additive was also demonstrated by the fact that three atropisomers, 1,1'-binaphthyl-2,2'-diyl hydrogen phosphate, 1.1'-binaphthyl-2,2'-diol, and Troger's base, and several neutral analytes were also successfully enantioresolved under these conditions. The separation mechanism seems to involve inclusion complexation.
Stalcup
A M
AM
Department of Chemistry, University of Hawaii-Manoa, Honolulu, Hawaii 96822, USA.
Gahm
K H
KH
D003505:Cyclodextrins / Q000737:chemistry*; D019075:Electrophoresis, Capillary / Q000379:methods*; D004364:Pharmaceutical Preparations / Q000302:isolation & purification; D013237:Stereoisomerism; D013431:Sulfates / Q000737:chemistry
D003505:Cyclodextrins; D004364:Pharmaceutical Preparations; D013431:Sulfates