A sulfated cyclodextrin chiral stationary phase for high-performance liquid chromatography.
A new sulfated beta-cyclodextrin (degree of substitution approximately 13-14/cyclodextrin) bonded chiral stationary phase (CSP) for high-performance liquid chromatography is introduced. The novel CSP was used to resolve a number of enantiomeric pairs, including antihistamines, antidepressants and phenylhydantoins, using HPLC under a variety of mobile phase conditions. Among the 33 analytes successfully enantioresolved, all but six had some amine functionality. Generally, the best separations were obtained for analytes in which the stereogenic center was either incorporated in a ring system or positioned between two aromatic rings. Retention seemed to arise from either inclusion complexation or electrostatic interactions. Ionic strength and pH were found to influence chiral recognition.
Stalcup
A M
AM
Department of Chemistry, University of Hawaii-Manoa, Honolulu 96822, USA.
Gahm
K H
KH
D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D003505:Cyclodextrins / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D009994:Osmolar Concentration; D004364:Pharmaceutical Preparations / Q000302:isolation & purification; D013237:Stereoisomerism; D013431:Sulfates / Q000737:chemistry
D003505:Cyclodextrins; D004364:Pharmaceutical Preparations; D013431:Sulfates