Electrophoresis 2007-08-01

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.

Kimberly A Kahle, Joe P Foley

Index: Electrophoresis 28(17) , 3024-40, (2007)

Full Text: HTML

Abstract

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).


Related Compounds

Related Articles:

Bioplastics from feather quill.

2011-10-10

[Biomacromolecules 12(10) , 3826-32, (2011)]

Separation of corticosteroids by microemulsion EKC with diethyl L-tartrate as the oil phase.

2007-10-01

[Electrophoresis 28(20) , 3691-6, (2007)]

A practical and azide-free synthetic approach to oseltamivir from diethyl D-tartrate.

2010-05-07

[J. Org. Chem. 75(9) , 3125-8, (2010)]

Two-chiral component microemulsion EKC - chiral surfactant and chiral oil. Part 2: diethyl tartrate.

2007-08-01

[Electrophoresis 28(15) , 2644-57, (2007)]

Total synthesis of broussonetine F: the orthoamide Overman rearrangement of an allylic diol.

2011-02-18

[Org. Lett. 13(4) , 616-9, (2011)]

More Articles...