Influence of microemulsion chirality on chromatographic figures of merit in EKC: results with novel three-chiral-component microemulsions and comparison with one- and two-chiral-component microemulsions.
Novel microemulsion formulations containing all chiral components are described for the enantioseparation of six pairs of pharmaceutical enantiomers (atenolol, ephedrine, metoprolol, N-methyl ephedrine, pseudoephedrine, and synephrine). The chiral surfactant dodecoxycarbonylvaline (DDCV, R- and S-), the chiral cosurfactant S-2-hexanol, and the chiral oil diethyl tartrate (R- and S-) were combined to create four different chiral microemulsions, three of which were stable. Results obtained for enantioselectivity, efficiency, and resolution were compared for the triple-chirality systems and the single-chirality system that contained chiral surfactant only. Improvements in enantioselectivity and resolution were achieved by simultaneously incorporating three chiral components into the aggregate. The one-chiral-component microemulsion provided better efficiencies. Enantioselective synergies were identified for the three-chiral-component nanodroplets using a thermodynamic model. Additionally, two types of dual-chirality systems, chiral surfactant/chiral cosurfactant and chiral surfactant/chiral oil, were examined in terms of chromatographic figures of merit, with the former providing much better resolution. The two varieties of two-chiral-component microemulsions gave similar values for enantioselectivity and efficiency. Lastly, the microemulsion formulations were divided into categories based on the number of chiral microemulsion reagents and the average results for each pair of enantiomers were analyzed for trends. In general, enantioselectivity and resolution were enhanced while efficiency was decreased as more chiral components were used to create the pseudostationary phase (PSP).
Kahle
Kimberly A
KA
Department of Chemistry, Drexel University, Philadelphia, PA 19104, USA.
Foley
Joe P
JP
D019075:Electrophoresis, Capillary / Q000379:methods; D004655:Emulsions; D004983:Ethanolamines / Q000737:chemistry*; D011412:Propanolamines / Q000737:chemistry*; D013237:Stereoisomerism; D013501:Surface-Active Agents / Q000737:chemistry*; D013644:Tartrates / Q000737:chemistry; D013816:Thermodynamics; D014633:Valine / Q000031:analogs & derivatives* / Q000737:chemistry
D004655:Emulsions; D004983:Ethanolamines; D011412:Propanolamines; D013501:Surface-Active Agents; D013644:Tartrates; C104188:N-dodecoxycarbonylvaline; D014633:Valine; C064501:diethyl tartrate