Use of chiral zwitterionic surfactants for enantiomeric resolutions by capillary electrophoresis

Hadley, Mark R.; Harrison, Mark; Hutt, Andrew J.

doi:10.1002/elps.200305467

Cited by 12 publications

(6 citation statements)

References 22 publications

(24 reference statements)

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“…The solvent was evaporated and the crude product was recrystallized from absolute ethanol. The structure was confirmed by 1 H, 13 …”

Section: Synthesis Of the Chiral Selectorsupporting

confidence: 62%

“…In recent times, CE has emerged as an efficient analytical technique for the enantiomeric analysis in pharmaceutical science [1][2][3][4][5] and for various applications in bioanalytical sciences [6][7][8]. Enantioselective separation techniques in CE are not only used for the enantioseparation of drugs and pharmaceuticals, they have also been applied to analyze chiral pollutants [9], and foods and beverages [10,11].…”

Section: Introductionmentioning

confidence: 99%

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Enantiomeric separations of binaphthyl derivatives by capillary electrophoresis using N‐(2‐hydroxydodecyl)‐L‐threonine as chiral selector: Effect of organic additives

Ghosh

Dey

2008

Electrophoresis

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The chiral selectivity of a novel amphiphile, N-(2-hydroxydodecyl)-L-threonine (2-HDT), was evaluated for enantiomeric resolution of three binaphthyl derivatives (+/-)-1,1'-bi-2-naphthol, (+/-)-1,1'-binaphthyl-2,2'-diamine, and (+/-)-1,1'-binaphthyl-2,2'-diylhdrogen phosphate (BNP) by micellar EKC. The effects of three organic modifiers, methanol, isopropanol, and acetonitrile, on the separations of enantiomers of these compounds were investigated. Separation of enantiomers could be achieved in relatively dilute solutions of the pure surfactant. However, best separations of enantiomers were obtained only in the presence of 10% v/v acetonitrile. Enantiomeric impurity in nonracemic mixtures of R- and S-forms of BNP was determined.

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“…The solvent was evaporated and the crude product was recrystallized from absolute ethanol. The structure was confirmed by 1 H, 13 …”

Section: Synthesis Of the Chiral Selectorsupporting

confidence: 62%

Section: Introductionmentioning

confidence: 99%

Enantiomeric separations of binaphthyl derivatives by capillary electrophoresis using N‐(2‐hydroxydodecyl)‐L‐threonine as chiral selector: Effect of organic additives

Ghosh

Dey

2008

Electrophoresis

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“…Following the research, the concentration of phosphate buffer (50, 100, 120 mM, pH 3.0) was evaluated to investigate its effect on the efficiency of enantioresolution and also the migration times. Increasing the buffer concentration leads to the reduction of the EOF and consequently increasing the current and the temperature (producing joule heating) and finally losing the resolution . Based on the observations, the optimum buffer concentration 100 mM was selected for further analyses.…”

Section: Resultsmentioning

confidence: 99%

Evaluation of the synergistic effect with amino acids for enantioseparation of basic drugs using capillary electrophoresis

et al. 2018

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The synergistic effect of two acidic amino acids, aspartic and glutamic acid, on the electrophoretic enantioseparation of four basic drugs was evaluated in the BGE containing a CD and at different pHs. Chlorpheniramine, hydroxyzine, propranolol and tramadol were used as the basic model drugs. However, no enantioseparations were achieved with a BGE containing sole amino acid, but the combined use of an acidic amino acid and a CD showed improved enantioseparations (synergistic effect) compared with the single CD system. The results demonstrated that at optimized pH, the electrostatic interactions of the anionic amino acids with the positively charged basic drugs could result in a decrease of the analyte migration velocity and it consequently improved the enantioseparation. The effective parameters such as the amino acid and chiral selector type and concentration, buffer pH, applied voltage, and capillary temperature were optimized. Favorable enantiomeric resolution and migration times of the model drugs were achieved with a 100 mM phosphate buffer solution (pH 3.0) containing 5.0 mM HP-α-CD/HP-β-CD and 20 mM aspartic acid with an 18 kV applied voltage at 25°C. H NMR experiments were also carried out in a mixture of an analyte and CD in the absence and presence of aspartic acid. The NMR results were consistent with the results obtained by CE which showed the synergistic effect of amino acid.

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“…Polar groups of ILs are suitable for HILIC [77][78][79]. Specific structures have been used for enantiomer separations [80][81][82][83]. Furthermore, ILs have been used to synthesize monolithic columns, and the incorporation of ILs in porous monoliths increased their selectivity [84,85].…”

Section: Typical Structures Of Bonded-phase For Hilicmentioning

confidence: 99%

Fundamental Properties of Packing Materials for Liquid Chromatography

Hanai¹

2019

Separations

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The high performance of chemically-modified silica gel packing materials is based on the utilization of pure silica gels. Earlier silica gels used to be made from inorganic silica; however, nowadays, silica gels are made from organic silanes. The surface smoothness and lack of trace metals of new silica gels permits easy surface modifications (chemical reactions) and improves the reproducibility and stability. Sharpening peak symmetry is based on developing better surface modification methods (silylation). Typical examples can be found in the chromatography of amitriptyline for silanol testing and that of quinizarin for trace metal testing. These test compounds were selected and demonstrated sensitive results in the measurement of trace amounts of either silanol or trace metals. Here, we demonstrate the three-dimensional model chemical structures of bonded-phase silica gels with surface electron density for easy understanding of the molecular interaction sites with analytes. Furthermore, a quantitative explanation of hydrophilic and hydrophobic liquid chromatographies was provided. The synthesis methods of superficially porous silica gels and their modified products were introduced.

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Use of chiral zwitterionic surfactants for enantiomeric resolutions by capillary electrophoresis

Cited by 12 publications

References 22 publications

Enantiomeric separations of binaphthyl derivatives by capillary electrophoresis using N‐(2‐hydroxydodecyl)‐L‐threonine as chiral selector: Effect of organic additives

Enantiomeric separations of binaphthyl derivatives by capillary electrophoresis using N‐(2‐hydroxydodecyl)‐L‐threonine as chiral selector: Effect of organic additives

Evaluation of the synergistic effect with amino acids for enantioseparation of basic drugs using capillary electrophoresis

Fundamental Properties of Packing Materials for Liquid Chromatography

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