Chiral separations by capillary zone electrophoresis: Present state of the art

Vespalec, Radim; Boček, Petr

doi:10.1002/elps.1150180603

Cited by 67 publications

(28 citation statements)

References 240 publications

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“…Thus, separation systems with the affinity selectors show low attractivity for practical applications. Previous general [3, 7,10] and specialized [19,28,86] review articles are recommended for more detailed information on these selectors.…”

Section: Affinity Chiral Selectorsmentioning

confidence: 99%

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Chiral separations in capillary electrophoresis

Vespalec

Boček

1999

Electrophoresis

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Section: Affinity Chiral Selectorsmentioning

confidence: 99%

“…They review either the partial time periods [1±10] or the particular aspects of the practical utilization of electrophoretic chiral separations [11±30]. Two of them [3,10] have an almost complete list of original papers published up to the end of 1996.…”

Section: Introductionmentioning

confidence: 99%

Chiral separations in capillary electrophoresis

Vespalec

Boček

1999

Electrophoresis

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“…Besides the major HPLC method, cyclodextrin-modified capillary zone electrophoresis (CZE) is enjoying increasing popularity. 4,5 In contrast to HPLC, in which chiral selectors are immobilized to the solid support, CZE shows many advantages by dissolving chiral selector in separation buffer, such as simplification, high efficiency, reduced analysis time, and smaller sample volumes. In CZE, borate buffers were widely used for the separation of carbohydrates, glycoproteins, nucleosides, and other compounds of biological interest.…”

Section: Introductionmentioning

confidence: 99%

Chiral Separation of Synthetic Vicinal Diol Compounds by Capillary Zone Electrophoresis with Borate Buffer and b-Cyclodextrin as Buffer Additive

et al. 2006

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The osmium-catalyzed asymmetric dihydroxylation (AD) of olefins is one of the most widely used methods for the synthesis of chiral vicinal diols, which are the synthetic intermediates of chiral drugs, natural products and fine chemicals. [1][2][3] For this reason, considerable and continuous efforts have been made to improve the optical purity of the resulting diols with the desired absolute configuration. 2,3 Similarly, the enantioselectivity estimation of a increasing number of chiral catalysts demands convenient, fast and sensitive methods to measure enantiomeric excesses and impurities of the chiral vicinal diol products. Besides the major HPLC method, cyclodextrin-modified capillary zone electrophoresis (CZE) is enjoying increasing popularity. 4,5 In contrast to HPLC, in which chiral selectors are immobilized to the solid support, CZE shows many advantages by dissolving chiral selector in separation buffer, such as simplification, high efficiency, reduced analysis time, and smaller sample volumes. In CZE, borate buffers were widely used for the separation of carbohydrates, glycoproteins, nucleosides, and other compounds of biological interest. [6][7][8][9][10][11][12][13] The phenomenon of borate complexation has been extensively studied and the principle of mixed borate-cyclodextrin complexation has been found to be a useful approach for the chiral separation of neutral compounds with diol structures. [6][7][8][9] For neutral analytes in the CZE separation mode, enantioseparation is not achievable with neutral CDs unless the electrophoretic system is modified with the use of a buffer system containing CD which can form charged complexes with analytes or with the addition of charged CDs in a buffer system. In those studies, to the best of our knowledge, so far only two articles on the enantioseparation of vicinal diols by the neutral cyclodextrin-modified capillary electrophoresis have been reported. 14,15 Moreover, the enantioseparation of hydrobenzoin, which is a 1,2-diol compound, and structurally related benzoin compounds have been achieved using charged CDs alone or mixed with neutral CDs as chiral selectors. 16,17 Unfortunately, no detailed information on the enantioseparation of typical vicinal diol compounds was provided. Thus, enantioseparation and migration behavior of typical vicinal diol compounds in the presence of borate complexation need to be explored further.In this study, the optimum conditions for the separation of six 1,2-diols synthesized in our laboratory according to literature methods 18,19 using native β-CD by CZE were described. Especially, the enantioseparation and migration behavior of several 1,2-diols, such as 1-(3-chlorophenyl)-1,2-ethanediol, 1-methyl-1-phenyl-1,2-ethanediol, 2-methyl-1-phenyl-1,2-ethanediol and 1-naphthyl-1,2-ethanediol, were firstly explored with neutral β-CD as a chiral selector in a borate buffer at an alkaline pH. For our studies, the influences of the concentration of β-CD, the pH of borate buffer and the buffer concentration on the chiral separation we...

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“…the chiral selector (SO) to the background electrolyte Quinine has been used as a chiral solvating agent [1][2][3][4]. Unfortunately, some of these chiral selectors, in nuclear magnetic resonance (NMR) studies [7], as used successfully on stationary phases in chiral higha chiral ion-pairing agent for enantioseparation in performance liquid chromatography (HPLC) have HPLC [8,9] as well as in capillary electrochromaonly limited solubility in aqueous buffers which are tography (CEC) [10] and as a selector immobilized generally used in CE.…”

Section: Introductionmentioning

confidence: 99%

“…These simultaneously acting multiple interactions can be seen as a basis for the high stereoselectivity potential shown by these SOs. Moreover, the introduction of a bulky alkyl substituent at the carbamate function (2) turned out to be advantageous for a further increase DNB (3,5-dinitrobenzoyl), (3) DNZ (3,5-dinitrobenzyloxycar-in stereoselectivity [13,14].…”

Section: Introductionmentioning

confidence: 99%

Non-aqueous capillary electrophoretic enantioseparation of N-derivatized amino acids using cinchona alkaloids and derivatives as chiral counter-ions

Piette

Fillet

Lindner

et al. 2000

Journal of Chromatography A

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A non-aqueous capillary electrophoretic method developed with quinine and tert.-butyl carbamoylated quinine as chiral selectors for the enantioseparation of N-protected amino acids was applied to the investigation of other quinine derivatives as chiral additives. The optimum composition of the background electrolyte was found to be 12.5 mM ammonia, 100 mM octanoic acid and 10 mM chiral selector in an ethanol-methanol (60:40, v / v) mixture. Under these conditions, a series of chiral acids, as various benzoyl, 3,5-dinitrobenzoyl and 3,5-dinitrobenzyloxycarbonyl amino acid derivatives were investigated with regards to selectand-selector relationships and enantioselectivity employing quinine, quinidine, cinchonine, cinchonidine, tert.-butyl carbamoylated quinine, tert.-butyl carbamoylated quinidine, dinitrophenyl carbamoylated quinine and cyclohexyl carbamoylated quinine as chiral selector.

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Chiral separations by capillary zone electrophoresis: Present state of the art

Cited by 67 publications

References 240 publications

Chiral separations in capillary electrophoresis

Chiral separations in capillary electrophoresis

Chiral Separation of Synthetic Vicinal Diol Compounds by Capillary Zone Electrophoresis with Borate Buffer and b-Cyclodextrin as Buffer Additive

Non-aqueous capillary electrophoretic enantioseparation of N-derivatized amino acids using cinchona alkaloids and derivatives as chiral counter-ions

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