Study of a new chiral selector: Sodium arsenyl-(l)-(+) tartrate for capillary electrophoresis

Tong, Man Yung; Payagala, Tharanga; Perera, S. Kusum; MacDonnell, Frederick M.; Armstrong, Daniel W.

doi:10.1016/j.chroma.2009.09.003

Cited by 10 publications

(10 citation statements)

References 43 publications

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“…The separation of the chloroquine enantiomers (Fig. 1) has been reported using charged CD derivatives as chiral selectors in acidic background electrolytes 20–23 as well as less frequently used additives such as human serum albumin 26, colominic acid 25, or arsenyl‐ L ‐(+)‐tartrate 27. Due to the commercial availability, sulfated β‐CD and SBE‐β‐CD were evaluated.…”

Section: Resultsmentioning

confidence: 99%

“…The CE enantioseparation of chloroquine has been achieved in the presence of various CDs as chiral selectors including sulfated β‐CD 20–22, sulfobutylether‐β‐CD (SBE‐β‐CD) 23 or a mixtures of two γ‐CD derivatives, either hydroxypropyl‐γ‐CD and carboxymethyl‐γ‐CD or hydroxypropyl‐γ‐CD and octakis(6‐ O ‐sulfo)‐γ‐CD 24. Furthermore, chloroquine enantioseparations in the presence of the polysaccharide colominic acid 25, human serum albumin 26, and arsenyl‐ L ‐(+)‐tartrate 27 have been published. However, none of the CE assays has been used for the determination of the stereoisomeric purity of the chloroquine enantiomers.…”

Section: Introductionmentioning

confidence: 99%

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Development and validation of a capillary electrophoresis assay for the determination of the stereoisomeric purity of chloroquine enantiomers

Scriba

2011

Electrophoresis

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A stereoselective CE assay for the determination of the enantiomeric purity of (R)-(-)-chloroquine and (S)-(+)-chloroquine was developed and validated. The separations were performed in a 50.2/40 cm uncoated fused silica capillary at 20°C using a 100 mM sodium phosphate buffer, pH 2.5, containing 30 mg/mL sulfobutylether(VII)-β-cyclodextrin as background electrolyte operated at an applied voltage of -25 kV and 20°C. The detection wavelength was 225 nm. Carbamazepine was used as internal standard. The assay was validated in the range of 0.05-1.0% for the respective minor chloroquine enantiomer based on a concentration of 3 mg/mL of the major enantiomer, either (R)-(-)-chloroquine or (S)-(+)-chloroquine. The method was applied to analyze the stereoisomeric purity of synthetic samples of the chloroquine enantiomers.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Development and validation of a capillary electrophoresis assay for the determination of the stereoisomeric purity of chloroquine enantiomers

Scriba

2011

Electrophoresis

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“…Unlike HPLC using chiral stationary phases, enantiomeric separations in CE are accomplished by adding the chiral selector into the run buffer. Although there are a wide number of chiral selectors applicable to CE, cyclodextrins and their derivatives dominate in CE for enantiomeric separations …”

Section: Introductionmentioning

confidence: 99%

“…Although there are a wide number of chiral selectors applicable to CE, cyclodextrins and their derivatives dominate in CE for enantiomeric separations. 29 To test the effectiveness of cyclodextrin and cyclofructan chiral selectors toward the enantiomeric separation of chiral synthetic intermediates of natural products, a set of probe analytes based on a 4,5,6,7-tetrahydrobenzimidazole (THB) scaffold with benzyl protection at the N1 position and varying substituents at the 5-, 6-, and 7-positions on the tetrahydrobenzimidazole were evaluated ( Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

The Enantiomeric Separation of Tetrahydrobenzimidazoles Cyclodextrins‐ and Cyclofructans

Perera

Doundoulakis

et al. 2012

Chirality

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High performance liquid chromatography (HPLC) and capillary electrophoresis (CE) were used to examine the enantiomeric separation of a series of 17 racemic tetrahydrobenzimidazole analytes. These compounds were prepared as part of a synthetic program directed towards a select group of pyrrole-imidazole alkaloids. This group of natural products has a unique framework of pyrrole- and guanidine-containing fused rings which can be constructed through the intermediacy of a tetrahydrobenzimidazole scaffold. Several bonded cyclodextrin- (both native and derivatized) and derivatized cyclofructan-based chiral stationary phases were evaluated for their ability to separate these racemates via HPLC. Similarly, several cyclodextrin derivatives and derivatized cyclofructan were evaluated for their ability to separate this set of chiral compounds via CE. Enantiomeric selectivity was observed for the entire set of racemic compounds using HPLC with resolution values up to 3.0. Among the 12 different CSPs, enantiomeric recognition was most frequently observed with the Cyclobond RN and LARIHC CF6-P, while the Cyclobond DMP yielded the greatest number of baseline separations. Fifteen of the analytes showed enantiomeric recognition in CE with resolution values as high as 5.0 and hydroxypropyl-γ-cyclodextrin was the most effective chiral additive.

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“…Due to its high efficiency, simplicity, rapidity, and low consumption of samples, CE is considered as a universal technology among the modern separation methods particularly for enantioseparations . Since the chiral enantiomers possess same charge densities, the separation principle of zonal electrophoretic which based on the different migration velocities of analytes with different charge densities is unsuitable for enantioseparation.…”

Section: Introductionmentioning

confidence: 99%

Label‐free aptamer‐based partial filling technique for enantioseparation and determination of dl‐tryptophan with micellar electrokinetic chromatography

et al. 2012

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In this study, a simple and reproducible method for enantioseparation and determination of dl-tryptophan (DL-Trp) was developed by using a partial filling technique in combination with MEKC. The corresponding L-Trp specific DNA aptamer was used as a chiral selector. Sodium cholate was used to form the chiral micelles and to enhance the enantioseparation of the enantiomers. Effects of aptamer concentration, filling time, buffer composition, and separation voltage on the enantioseparation were evaluated. The Mg(2+) and Na(+) concentration in separation buffer was found to effectively affect the separation efficiency and reproducibility. Under the optimal conditions, D- and L-Trp were completely enantioseparated in less than 9 min. This aptamer-based partial-filling approach has the potential to be extended to the separation of other enantiomers after the replacement of corresponding specific aptamers.

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Study of a new chiral selector: Sodium arsenyl-(l)-(+) tartrate for capillary electrophoresis

Cited by 10 publications

References 43 publications

Development and validation of a capillary electrophoresis assay for the determination of the stereoisomeric purity of chloroquine enantiomers

Development and validation of a capillary electrophoresis assay for the determination of the stereoisomeric purity of chloroquine enantiomers

The Enantiomeric Separation of Tetrahydrobenzimidazoles Cyclodextrins‐ and Cyclofructans

Label‐free aptamer‐based partial filling technique for enantioseparation and determination of dl‐tryptophan with micellar electrokinetic chromatography

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