Effect of oil substitution in chiral microemulsion electrokinetic chromatography.
In a previous publication (Pascoe, R., Foley, J. P., Analyst 2002, 127, 710-714), a novel chiral microemulsion based on 1.0% w/v dodecoxycarbonylvaline (DDCV), 0.50% v/v ethyl acetate and 1.2% v/v 1-butanol, was shown to provide rapid enantiomeric separations of various pharmaceutical compounds. The two deficiencies noted with this method were that the peak shapes obtained were asymmetric and the efficiencies were lower than those previously obtained using DDCV micelles (Peterson, A. G., Ahuja, E. S., Foley, J. P., J. Chromatogr. B 1996, 683, 15-28). This study examines the use of three alternative low-interfacial-tension oils (methyl acetate, methyl propionate, and methyl formate), in combination with DDCV, to characterize their effect on the elution range, efficiency, resolution, and enantioselectivity of various pharmaceutical enantiomers. The oils were evaluated in both the same volume percentage and the same molar concentration as ethyl acetate in the original DDCV microemulsion system. Including ethyl acetate, a total of seven microemulsion systems were examined. For the compounds that were separated, average enantioselectivities ranged from 1.09 to 1.28, with corresponding efficiencies of 14,000-20,000. While some interesting differences were observed, ethyl acetate still proved to be the most advantageous in terms of enantioselectivity, resolution, and elution range.
Mertzman
Melissa D
MD
Department of Chemistry, Drexel University, Philadelphia, PA 19104, USA.
Foley
Joe P
JP
D000085:Acetates / Q000737:chemistry; D020374:Chromatography, Micellar Electrokinetic Capillary / Q000379:methods*; D004655:Emulsions / Q000737:chemistry*; D004809:Ephedrine / Q000302:isolation & purification; D009821:Oils / Q000737:chemistry*; D004364:Pharmaceutical Preparations / Q000032:analysis* / Q000737:chemistry; D013237:Stereoisomerism; D013501:Surface-Active Agents / Q000737:chemistry; D014633:Valine / Q000031:analogs & derivatives*
D000085:Acetates; D004655:Emulsions; D009821:Oils; D004364:Pharmaceutical Preparations; D013501:Surface-Active Agents; C104188:N-dodecoxycarbonylvaline; C007650:ethyl acetate; D004809:Ephedrine; D014633:Valine