Use of a microemulsion system to incorporate a lipophilic chiral selector in electrokinetic capillary chromatography

Aiken, Joseph H.; Huie, Carmen W.

doi:10.1007/bf02278600

Cited by 93 publications

(65 citation statements)

References 21 publications

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“…Three recent reviews on MEEKC have included chiral applications [55][56][57]. The first separation via chiral MEEKC was reported by Aiken and Huie et al [58] in 1993 and utilized a chiral oil, (2R, 3R)-di-n-butyl tartrate, in conjunction with an achiral surfactant (SDS) and achiral cosurfactant (1-butanol) to achieve a selectivity of 2.6 for the enantiomers of ephedrine. It was also shown that the presence of 1-butanol (the cosurfactant) was essential -no enantioseparation could be achieved when it was omitted.…”

Section: Microemulsionsmentioning

confidence: 99%

Review of aqueous chiral electrokinetic chromatography (EKC) with an emphasis on chiral microemulsion EKC

Kahle

Foley

2007

Electrophoresis

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Review of aqueous chiral electrokinetic chromatography (EKC) with an emphasis on chiral microemulsion EKCThe separation of enantiomers using electrokinetic chromatography (EKC) with chiral microemulsions is comprehensively reviewed through December 1, 2006. Aqueous chiral EKC separations based on other pseudostationary phases such as micelles and vesicles or on other chiral selectors such as CDs, crown ethers, glycopeptides, ligand exchange moeities are also reviewed from both mechanistic and applications perspective for the period of

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Section: Microemulsionsmentioning

confidence: 99%

Review of aqueous chiral electrokinetic chromatography (EKC) with an emphasis on chiral microemulsion EKC

Kahle

Foley

2007

Electrophoresis

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“…Chiral separations can be accomplished with MEEKC by incorporating one or more chiral entities into the microemulsion formulation. The first such publication described chiral selectivity achieved by using an aggregate system consisting of an achiral surfactant, an achiral cosurfactant, and a chiral oil (dibutyl tartrate) [49]. Several investigations in chiral MEEKC have been performed by our group with the surfactant dodecoxycarbonylvaline (DDCV) serving as the only chiral selectand in the PSP formulation and have focused on variations of surfactant concentration [50], buffer identity [50], oil identity [51], temperature [52], and cosurfactant identity [53].…”

Section: Introductionmentioning

confidence: 99%

Two‐chiral component microemulsion EKC – chiral surfactant and chiral oil. Part 2: Diethyl tartrate

Kahle

Foley

2007

Electrophoresis

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In this second study on dual-chirality microemulsions containing a chiral surfactant and a chiral oil, a less hydrophobic and lower interfacial tension chiral oil, diethyl tartrate, is employed (Part 1, Foley, J. P. et al.., Electrophoresis, DOI: 10.1002/elps.200600551). Six stereochemical combinations of dodecoxycarbonylvaline (DDCV: R, S, or racemic, 2.00% w/v), racemic 2-hexanol (1.65% v/v), and diethyl tartrate (D, L, or racemic, 0.88% v/v) were examined as pseudostationary phases (PSPs) for the enantioseparation of six chiral pharmaceutical compounds: pseudoephedrine, ephedrine, N-methyl ephedrine, metoprolol, synephrine, and atenolol. Average efficiencies increased with the addition of a chiral oil to R-DDCV PSP formulations. Modest improvements in resolution and enantioselectivity (alpha(enant)) were achieved with two-chiral-component systems over the one-chiral-component microemulsion. Slight enantioselective synergies were confirmed using a thermodynamic model. Results obtained in this study are compared to those obtained in Part 1 as well as those obtained with chiral MEEKC using an achiral, low-interfacial-tension oil (ethyl acetate). Dual-chirality microemulsions with the more hydrophobic oil dibutyl tartrate yielded, relative to diethyl tartrate, higher efficiencies (100,000-134,000 vs. 80,800-94,300), but lower resolution (1.64-1.91 vs. 2.08-2.21) due to lower enantioselectivities (1.060-1.067 vs. 1.078-1.081). Atenolol enantiomers could not be separated with the dibutyl tartrate-based microemulsions but were partially resolved using diethyl tartrate microemulsions. A comparable single-chirality microemulsion based on the achiral oil ethyl acetate yielded, relative to diethyl tartrate, lower efficiency (78 300 vs. 91 600), higher resolution (1.99 vs. 1.83), and similar enantioselectivities.

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“…16 They used a chiral oil, (2R,3R)-di-n-butyl tartrate, along with an achiral surfactant (sodium dodecyl sulfate, SDS) and an achiral cosurfactant (1-butanol). A chiral microemulsion was made up and the resolution of ephedrine isomers was demonstrated.…”

Section: Introductionmentioning

confidence: 99%

(S)-(+)-2-Octanol as a Chiral Oil Core for the Microemulsion Electrokinetic Chromatographic Separation of Chiral Basic Drugs

Threeprom

2007

ANAL. SCI.

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Use of a microemulsion system to incorporate a lipophilic chiral selector in electrokinetic capillary chromatography

Cited by 93 publications

References 21 publications

Review of aqueous chiral electrokinetic chromatography (EKC) with an emphasis on chiral microemulsion EKC

Review of aqueous chiral electrokinetic chromatography (EKC) with an emphasis on chiral microemulsion EKC

Two‐chiral component microemulsion EKC – chiral surfactant and chiral oil. Part 2: Diethyl tartrate

(S)-(+)-2-Octanol as a Chiral Oil Core for the Microemulsion Electrokinetic Chromatographic Separation of Chiral Basic Drugs

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