Application of tetraoxadiaza-crown ether derivatives as chiral selector modifiers in capillary electrophoresis

Iványi, Tímea; Pál, Kornélia; Lázár, István; Massart, D.L.; Heyden, Yvan Vander

doi:10.1016/j.chroma.2003.11.097

Cited by 32 publications

(28 citation statements)

References 29 publications

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“…More recently, the trend has been to create single-isomer derivatized CDs in an attempt to reduce batch-to-batch variability and improve reproducibility [21]. Other chiral selectors include [5,22]: proteins [23,24], crown ethers [25], oligosaccharides, polysaccharides, macrocyclic antibiotics [26], and surfactant aggregates [27,28] (micelles (monomeric [29,30] and polymeric [31][32][33][34]), vesicles [35,36], and microemulsions (vide infra)). Important aspects to consider when choosing a chiral selectand are solubility, UV transparency, and whether or not other stereoisomers are available for elution order reversal [37].…”

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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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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“…Resolution was found to be highly dependent on buffer identity and concentration. The combination of CDs with chiral or achiral crown ethers also proved to be synergistic [5,6,53,113,114]. Horimai et al [115] investigated the chiral resolution of some quinolone drugs using ligand-exchange and host-guest interactions.…”

Section: Dual-selector Systemsmentioning

confidence: 97%

Chiral separations by capillary electrophoresis: Recent developments and applications

2006

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“…Such combinations can enhance or even enable chiral separation. A new class of crown ethers, tetraoxadiaza-crown ether derivatives, have been synthesized by Ivanyi et al [24]. These selectors did not show any chiral recognition ability individually, however, they enhanced the enantioselective effect of different cyclodextrins in dual selector systems.…”

Section: Capillary Zone Electrophoresismentioning

confidence: 98%

Recent advances in chiral separation principles in capillary electrophoresis and capillary electrochromatography

2004

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This review summarizes recent developments in chiral separation in capillary zone electrophoresis (CZE), electrokinetic chromatography (EKC), and capillary electrochromatography (CEC) covering literature published since the year 2000. New chiral selectors and innovative approaches for CE and CEC are introduced. Recent progress in column technology for CEC is highlighted and the development of new chiral stationary phases is discussed. This review is not dedicated to list applications but will focus on new developments.

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Application of tetraoxadiaza-crown ether derivatives as chiral selector modifiers in capillary electrophoresis

Cited by 32 publications

References 29 publications

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

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

Chiral separations by capillary electrophoresis: Recent developments and applications

Recent advances in chiral separation principles in capillary electrophoresis and capillary electrochromatography

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