Chiral separation of several amino acid derivatives by capillary zone electrophoresis with selectively acetylated β-cyclodextrin derivatives

Miura, Masaru; Kawamoto, Kiyotoshi; Funazo, Koichi; Tanaka, Minoru

doi:10.1016/s0003-2670(98)00396-1

Cited by 18 publications

(6 citation statements)

References 25 publications

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“…Therefore, some groups isolate the single isomers or synthesize selectively substituted derivatives. Selectively methylated and acetylated CDs were synthesized by Miura et al [342] and applied to the chiral separation of amino acids derivatives. A new uncharged CDderivative, cyanoethylated b-CD has recently been introduced by Aturki et al [343].…”

Section: Neutral CD Derivatives a Great Variety Of Neutral Derivativmentioning

confidence: 99%

Chiral separation by chromatographic and electromigration techniques. A Review

Gübitz

Schmid

2001

Biopharm & Drug Disp

225

135

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This review gives a survey of different chiral separation principles and their use in high-performance liquid chromatography (HPLC), gas chromatography (GC), supercritical fluid chromatography (SFC), thin-layer chromatography (TLC), capillary electrophoresis (CE) and capillary electrochromatography (CEC) highlighting new developments and innovative techniques. The mechanisms of the different separation principles are briefly discussed and some selected applications are shown.

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Section: Neutral CD Derivatives a Great Variety Of Neutral Derivativmentioning

confidence: 99%

Chiral separation by chromatographic and electromigration techniques. A Review

Gübitz

Schmid

2001

Biopharm & Drug Disp

225

135

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“…Miura et al synthesized selectively methylated [23] and acetylated [24] CDs and evaluated the different products for their ability to resolve Dns-amino acids, naphthalenesulfonylamino acids and naphthoylamino acids. The authors have shown that there are remarkable differences in selectivity between the methylated and acetylated CDs due to the difference in bulkiness and hydrogen-bonding ability.…”

Section: Neutral Cdsmentioning

confidence: 99%

Recent progress in chiral separation principles in capillary electrophoresis

2000

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This review summarizes recent developments in the field of chiral separations by electromigration techniques including capillary zone electrophoresis (CZE), capillary gel electrophoresis (CGE), isotachophoresis (ITP), electrokinetic chromatography (EKC), and capillary electrochromatography (CEC). This overview focuses on the development of new chiral selectors and the introduction of new techniques rather than applications of already established selectors and methods. The mechanisms of the different chiral separation principles are discussed.

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“…The degree and the site of methylation influences the properties such as solubility, complexation ability, and enantiorecognition of the CD, therefore it is of vital importance to gain as complete picture as possible on these features. The enantiorecognition ability of various methylated CDs has already been investigated previously; however, those studies did not cover the full set of the available CDs or did not use single chemical entities but mixtures of variously under‐/over‐methylated isomers . The effect of degree of methylation on the enantiomer migration order has also been shown for peptide enantiomers reviewed by G.K.E Scriba .…”

Section: Introductionmentioning

confidence: 99%

Comparative analysis of the full set of methylated β‐cyclodextrins as chiral selectors in capillary electrophoresis

et al. 2019

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Comparative analysis of the full set of methylated ␤-cyclodextrins as chiral selectors in capillary electrophoresisThe chiral separation ability of the full library of methylated-␤-cyclodextrins towards pharmacologically significant racemic drugs including basic compounds was studied by chiral CE. The syntheses of all the methylated, single isomer ␤-cyclodextrins were revised and optimized and the aqueous solubility of the derivatives was unambiguously established. The three most relevant commercially available methylated isomeric mixtures were also included in the screening, so a total of ten various methylated CDs were investigated. The effects of the selector concentration on the enantiorecognition properties at acidic pH were investigated. Among the dimethylated ␤-cyclodextrins, the heptakis (2,6-di-Omethyl)-␤-cyclodextrin isomer (2,6-DIMEB) resulted to be the most versatile chiral selector. Terbutaline was selected as a model compound for the in-depth investigation of host-guest enantiodiscrimination ability. The association constants between the two terbutaline enantiomers and 2,6-DIMEB were determined in order to support that the enantioseparation is driven by differences is host-guest binding. The migration order of the enantiomers was confirmed by performing spiking experiments with the pure enantiomers. 1D and 2D NMR spectroscopy was applied to the 2,3-, and 2,6-DIMEB/terbutaline systems to rationalize at molecular level the different enantioseparation ability of the dimethylated ␤-cyclodextrin selectors.

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Chiral separation of several amino acid derivatives by capillary zone electrophoresis with selectively acetylated β-cyclodextrin derivatives

Cited by 18 publications

References 25 publications

Chiral separation by chromatographic and electromigration techniques. A Review

Chiral separation by chromatographic and electromigration techniques. A Review

Recent progress in chiral separation principles in capillary electrophoresis

Comparative analysis of the full set of methylated β‐cyclodextrins as chiral selectors in capillary electrophoresis

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