Single isomer cyclodextrins as chiral selectors in capillary electrophoresis

Fejős, Ida; Kalydi, Eszter; Malanga, Milo; Benkovics, Gábor; Béni, Szabolcs

doi:10.1016/j.chroma.2020.461375

Cited by 50 publications

(45 citation statements)

References 217 publications

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“…Positively charged derivatized CDs as a quaternary ammonium CD also showed successful applications. Among others, hydroxypropyl derivatized CDs are claimed to have the best enantioseparation power for a wider variety of chiral compounds [ 6 , 52 , 53 , 54 , 55 ].…”

Section: Chiral Capillary Electrokinetic Chromatography Principle and Selectorsmentioning

confidence: 99%

“…The single isomer CDs are preferred for chiral separation to obtain reproducible results, but also to study aspects of the selector-analyte interactions and to better understand the experimental design of chiral CE separations [ 53 ].…”

Section: Chiral Capillary Electrokinetic Chromatography Principle and Selectorsmentioning

confidence: 99%

“…The CDs have been applied mostly as a single chiral selector, but also sometimes in a dual or multiple chiral system, as described below. Tuning of enantio-discrimination can be achieved by substitution of the single CD molecule, but also fine-tuning is possible by modifying the other separation conditions [ 53 ]. Cucinotta et al [ 57 ] synthesized and characterized a new capped derivative of β-CD.…”

Section: Chiral Capillary Electrokinetic Chromatography Principle and Selectorsmentioning

confidence: 99%

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Chiral Capillary Electrokinetic Chromatography: Principle and Applications, Detection and Identification, Design of Experiment, and Exploration of Chiral Recognition Using Molecular Modeling

et al. 2021

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This work reviews the literature of chiral capillary electrokinetic chromatography from January 2016 to March 2021. This is done to explore the state-of-the-art approach and recent developments carried out in this field. The separation principle of the technique is described and supported with simple graphical illustrations, showing migration under normal and reversed polarity modes of the separation voltage. The most relevant applications of the technique for enantioseparation of drugs and other enantiomeric molecules in different fields using chiral selectors in single, dual, or multiple systems are highlighted. Measures to improve the detection sensitivity of chiral capillary electrokinetic chromatography with UV detector are discussed, and the alternative aspects are explored, besides special emphases to hyphenation compatibility to mass spectrometry. Partial filling and counter migration techniques are described. Indirect identification of the separated enantiomers and the determination of enantiomeric migration order are mentioned. The application of Quality by Design principles to facilitate method development, optimization, and validation is presented. The elucidation and explanation of chiral recognition in molecular bases are discussed with special focus on the role of molecular modeling.

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Section: Chiral Capillary Electrokinetic Chromatography Principle and Selectorsmentioning

confidence: 99%

Section: Chiral Capillary Electrokinetic Chromatography Principle and Selectorsmentioning

confidence: 99%

Section: Chiral Capillary Electrokinetic Chromatography Principle and Selectorsmentioning

confidence: 99%

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Chiral Capillary Electrokinetic Chromatography: Principle and Applications, Detection and Identification, Design of Experiment, and Exploration of Chiral Recognition Using Molecular Modeling

et al. 2021

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“…The majority of commercially available CDs are randomly substituted ones, consisting of a complex mixture of isomers with various degrees and positions of substitution. As high reproducibility is essential in method development, there is an ever-growing tendency to use single isomer derivatives (SIDs) as chiral selectors [3,4], as those also facilitate the understanding of the chiral recognition mechanisms.…”

Section: Introductionmentioning

confidence: 99%

Single Isomer N-Heterocyclic Cyclodextrin Derivatives as Chiral Selectors in Capillary Electrophoresis

et al. 2021

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In order to better understand the chiral recognition mechanisms of positively charged cyclodextrin (CD) derivatives, the synthesis, the pKa determination by 1H nuclear magnetic resonance (NMR)-pH titration and a comparative chiral capillary electrophoretic (CE) study were performed with two series of mono-substituted cationic single isomer CDs. The first series of selectors were mono-(6-N-pyrrolidine-6-deoxy)-β-CD (PYR-β-CD), mono-(6-N-piperidine-6-deoxy)-β-CD (PIP-β-CD), mono-(6-N-morpholine-6-deoxy)-β-CD (MO-β-CD) and mono-(6-N-piperazine-6-deoxy)-β-CD (PIPA-β-CD), carrying a pH-adjustable moiety at the narrower rim of the cavity, while the second set represented by their quaternarized, permanently cationic counterparts: mono-(6-N-(N-methyl-pyrrolidine)-6-deoxy)-β-CD (MePYR-β-CD), mono-(6-N-(N-methyl-piperidine)-6-deoxy)-β-CD (MePIP-β-CD), mono-(6-N-(N-methyl-morpholine)-6-deoxy)-β-CD (MeMO-β-CD) and mono-(6-N-(4,4-N,N-dimethyl-piperazine)-β-CD (diMePIPA-β-CD). Based on pH-dependent and selector concentration-dependent comparative studies of these single isomer N-heterocyclic CDs presented herein, it can be concluded that all CDs could successfully be applied as chiral selectors for the enantiodiscrimination of several negatively charged and zwitterionic model racemates. The substituent-dependent enantiomer migration order reversal of dansylated-valine using PIP-β-CD contrary to PYP-β-CD, MO-β-CD and PIPA-β-CD was also studied by 1H- and 2D ROESY NMR experiments.

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“…Many technologies and methods have been developed for enantioselective analysis, including HPLC [11][12][13][14], CE [15][16][17][18], GC [19,20], supercritical fluid chromatography [21], and nuclear magnetic resonance (NMR) [22,23]. These methods have been widely applied and intensively investigated and developed over the past several decades.…”

Section: Introductionmentioning

confidence: 99%

Direct distinction of ibuprofen and flurbiprofen enantiomers by ion mobility mass spectrometry of their ternary complexes with metal cations and cyclodextrins in the gas phase

Yang

et al. 2021

J of Separation Science

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Enantiomeric drugs are widely used and play important roles in pharmaceuticals. Ion mobility spectrometry coupled with mass spectrometry technology provides a unique method for distinguishing the enantiomeric drugs, enantiomeric identification, and quantitation in the gas phase. In this study, enantiomeric molecules of ibuprofen and flurbiprofen were clearly recognized by forming host-guest complex ions using trapped ion mobility time-of-flight mass spectrometry. Ternary complex ions can be produced easily by electrospray ionization of the mixed solutions of ibuprofen, cyclodextrins, and CaCl 2 , LiCl, or NaCl, as well as flurbiprofen, cyclodextrins, and CaCl 2 . The relative contents of different chiral ibuprofens in a mixed solution were also quantitatively measured. This new method is a simple, effective, and a convenient enantioselective analysis method.

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Single isomer cyclodextrins as chiral selectors in capillary electrophoresis

Cited by 50 publications

References 217 publications

Chiral Capillary Electrokinetic Chromatography: Principle and Applications, Detection and Identification, Design of Experiment, and Exploration of Chiral Recognition Using Molecular Modeling

Chiral Capillary Electrokinetic Chromatography: Principle and Applications, Detection and Identification, Design of Experiment, and Exploration of Chiral Recognition Using Molecular Modeling

Single Isomer N-Heterocyclic Cyclodextrin Derivatives as Chiral Selectors in Capillary Electrophoresis

Direct distinction of ibuprofen and flurbiprofen enantiomers by ion mobility mass spectrometry of their ternary complexes with metal cations and cyclodextrins in the gas phase

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