Electrokinetic chromatography with 2-O-carboxymethyl-β-cyclodextrin as a moving “stationary” phase

Terabe, Shigeru; Ozaki, H.; Otsuka, Koji; Ando, Teiichi

doi:10.1016/s0021-9673(01)83299-4

Cited by 286 publications

(83 citation statements)

References 9 publications

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“…3 Many researchers focus their work on the development of novel methods concerning MEKC by using modifiers. For example, cyclodextrin-modified MEKC (CD-MEKC) [4][5][6][7] borate-complex EKC 8,9 and ion-exchange EKC 10,11 have been reported. Each of these methods has extended the application of MEKC to the analysis of various types of compounds.…”

mentioning

confidence: 99%

Reversal Behaviors of the Enantiomer Migration Order and the Stereo-selectivity of Cu(II) Complex with Amino Acid Enantiomers in Ligand Exchange-Micellar Electrokinetic Chromatography

et al. 2000

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Since the pioneering work of Terabe et al. 1,2 micellar electrokinetic chromatography (MEKC) has become a powerful technique for the analysis of both neutral and charged samples. 3 Many researchers focus their work on the development of novel methods concerning MEKC by using modifiers. For example, cyclodextrin-modified MEKC (CD-MEKC) 4-7 borate-complex EKC 8,9 and ion-exchange EKC 10,11 have been reported. Each of these methods has extended the application of MEKC to the analysis of various types of compounds. The mechanism of the ligand exchange was reported for the separation of dansyl amino acid enantiomers by liquid chromatography 12,13 and subsequently capillary electrophoresis. 13,14 Ligand exchange-micellar electrokinetic chromatography (LE-MEKC), a hybrid technique of the ligand exchange mechanism and MEKC, has been receiving increasing attention, because it offers the possibility of the simultaneous separation of optical isomers with the differences in the positional structure, such as o-, m-, p-enantiomers of amino acids, which contain a phenyl ring with different substituents 16 as well as positional and optical isomers of the tryptophan family. 17 Based on the ligand exchange mechanism, it is the difference in the stability constants that give the chiral separation of enantiomers. In other words, the EMO depends on the stability of the complex. Therefore, EMO can be predicted based on the stability of the complex. Conversely, the EMO can be applied in a study of complex stability.In order to explore the mechanism of LE-MEKC and to provide some scientific evidence for predicting and controlling the EMO or for studying the complex stability of a ternary Cu(II) complex with different amino acid enantiomers, it is significant to study the separation behavior of enantiomers in LE-MEKC. In fact, many works have thrown light on the reversal of the EMO. 14,15,18-22 Our previous work involved the separation behavior of amino acid enantiomers in LE-MEKC, 23 in which we discussed the reversal of EMO of amino acids and o-, m-and p-order of enantiomers with the introduction of micellar phases. In this paper we focus our study on the influence of ligand chirality, trans-and cis-conformation of 4-hydroxy group in hydroxyproline and the SDS micellar phase on the separation behavior when using different ligands of the proline family in LE-MEKC. Experimental InstrumentationThe CE instrumental setup involves a HEL5-30P2-TTu high voltage power supply (Matsusada Precision Devices Inc., Japan), a CE-971 UV detector (Jasco Corporation, Japan) and a C-R6A Chromatopac Recorder (Shimadzu, Japan). Separations were carried out in fused-silica capillaries (0.050 mm i.d.×0.375 mm o.d.) from GL Sciences Inc. (Japan) with a total length of 56 cm and an effective length of 40 cm. ChemicalsAll of the chemicals were of reagent grade and were used as Hachioji, Japan The dependence of the enantioselectivity and enantiomer migration order (EMO) on the chirality and stereo-conformation of ligands used for the chiral selectors of Cu(...

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Reversal Behaviors of the Enantiomer Migration Order and the Stereo-selectivity of Cu(II) Complex with Amino Acid Enantiomers in Ligand Exchange-Micellar Electrokinetic Chromatography

et al. 2000

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“…The use of cyclodextrins has been successfully applied to the separation of isomeric compounds (56), and to the optical resolution of racemic amino acid derivatives (57).…”

Section: Buffer Solution In Capillary Electrophoresismentioning

confidence: 99%

“…For example, a cyclodextrin derivative containing ionizing groups has been employed as a substitute for a charged micelle (56). In this case, the cyclodextrin derivative acts as a chromatographic phase as it is in the case of the micelle, although it constitutes a homogeneous solution.…”

Section: Buffer Solution In Capillary Electrophoresismentioning

confidence: 99%

High-Resolution Nanotechnique for Separation, Characterization, and Quantitation of Micro- and Macromolecules

Guzman

Hernández

Terabe

1990

ACS Symposium Series

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“…[1][2][3] Several CE studies have reported on the separation of enantiomers by employing cyclodextrin electrokinetic chromatography (CDEKC). [4][5][6][7][8][9][10][11] A wide range of native α-, β-, or γ-cyclodextrins (CDs) as well as charged and neutral CD derivatives are employed as chiral selectors. The optimization of an enantiomeric separation can be achieved by changing the type and/or the concentration of CDs, or the pH of the running buffer.…”

Section: Introductionmentioning

confidence: 99%

Rapid Enantioseparation of 1-Aminoindan by Microchip Electrophoresis with Linear-Imaging UV Detection

2005

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Chiral separations of 1-aminoindan (AI) by cyclodextrin electrokinetic chromatography (CDEKC) were investigated on microfluidic quartz chips. By using a microchip electrophoresis (MCE) instrument equipped with a linear-imaging UV detector, the separation process of the enantiomeric compounds was observed. When sulfated β-cyclodextrin was employed as a chiral selector, the baseline separation of AI could be achieved within 1 min with a high repeatability. The relative standard deviation of the migration time was less than 6%. The fastest separation was achieved in 14 s, utilizing a separation length of only 6.1 mm. These results show that the MCE analysis employing a linear imaging UV detector has a significant potential for fast chiral analysis.

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Electrokinetic chromatography with 2-O-carboxymethyl-β-cyclodextrin as a moving “stationary” phase

Cited by 286 publications

References 9 publications

Reversal Behaviors of the Enantiomer Migration Order and the Stereo-selectivity of Cu(II) Complex with Amino Acid Enantiomers in Ligand Exchange-Micellar Electrokinetic Chromatography

Reversal Behaviors of the Enantiomer Migration Order and the Stereo-selectivity of Cu(II) Complex with Amino Acid Enantiomers in Ligand Exchange-Micellar Electrokinetic Chromatography

High-Resolution Nanotechnique for Separation, Characterization, and Quantitation of Micro- and Macromolecules

Rapid Enantioseparation of 1-Aminoindan by Microchip Electrophoresis with Linear-Imaging UV Detection

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