Comparison of charged cyclodextrin derivatives for the chiral separation of atropisomeric polychlorinated biphenyls by capillary electrophoresis

García‐Ruiz, Carmen; Crego, Antonio L.; Marina, Marı́a Luisa

doi:10.1002/elps.200305465

Cited by 21 publications

(13 citation statements)

References 42 publications

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“…García-Ruiz et al [65] have also compared the use of different CDs for the chiral separation of the 19 atropisomeric PCBs. Anionic CDs, b-CD-phosphated, b-CD-sulfated, succinylated-g-CD (Succ-g-CD) and succinylatedb-CD (Succ-b-CD), and cationic CD, 6-monodeoxy-6- monoamino-b-CD (b-CD-NH 2 ) were tested.…”

Section: Chiral Analysis Of Pcbsmentioning

confidence: 99%

Chiral analysis of pollutants and their metabolites by capillary electromigration methods

et al. 2005

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Chiral analysis of pollutants and their metabolites by capillary electromigration methodsChiral separation of enantiomers is one of the most challenging tasks for any analytical technique including CE. Since the first report in 1985 showing the great possibilities of CE for the separation of chiral compounds, the amount of publications concerning this topic has quickly increased. Although chiral electromigration methods have mainly been used for enantioseparation of drugs and pharmaceuticals, they have also been applied to analyze chiral pollutants. This article intends to provide an updated overview, including works published till January 2005, on the principal applications of CE to the chiral analysis of pollutants and their metabolites, with especial emphasis on articles published in the last 10 years. The main advantages and drawbacks regarding the use of CE for chiral separation of pollutants are addressed including some discussion on the foreseen trends of electromigration procedures applied to chiral analysis of contaminants. IntroductionSeparation of chiral compounds is an interesting and challenging topic of research in many analytical chemistry areas, especially in the biomedical, pharmaceutical, and environmental fields where pure enantiomeric forms are widely required. It is already well-known that enantiomers, in spite of their very similar structure, when exposed to an identical biological environment can show very different biological activity. Furthermore, as a general rule, when the toxicological effect of an active substance is directly related to its desired biological activity, the most active isomer is usually the most toxic one Abbreviations: Allyl-TER, 1-allylterguride; ANDSA, 7-aminonaphthalene-1,3-disulfonic acid; ANSA, 5-aminonaphthalene-1-sulfonic acid; ANTS, 8-aminonaphthalene-1,3,6-trisulfonic acid; CA, chrysanthemic acid; CM-ª-CD, carboxymethylated-g-CD; CMBA, 2-(4-chlorophenyl)-3-methylbutanoic acid; 2,2-CPPA, 2-(2-chlorophenoxy)-propionic acid; 2,3-CPPA, 2-(3-chlorophenoxy)-propionic acid; 2,4-CPPA, 2-(4-chlorophenoxy)-propionic acid; â-CD-NH 2 , 6-monodeoxy-6-monoamino-b-CD; â-CD- (NH 3 )

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Section: Chiral Analysis Of Pcbsmentioning

confidence: 99%

Chiral analysis of pollutants and their metabolites by capillary electromigration methods

et al. 2005

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“…Enantiomers with planar or axial asymmetry suit the chiral recognition feature of CDs, and not only the enantiomers with central asymmetry. The chiral CE literature has already published such separations for polychlorinated biphenyls [27] and allenic acids [38]. CDs are able to separate enantiomers with heteroatomic chiral centers in CE (S, P, N, and Si) as have been published [26,39].…”

Section: Basic Physical Background Of Chiral Separation In Cementioning

confidence: 96%

“…This means, the neutral enantiomers can not be separated with neutral selectors, because the migration speed of the enantiomers is equal to EOF in both free and associated forms. The separation of neutral enantiomers generally requires charged selectors, or a combination of a neutral selector with charged achiral micelles [26,27].Equation (1) has some important consequences. The migration difference has an optimum as a function of concentration of chiral selectors, which was empirically demonstrated [28].…”

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confidence: 99%

The role of cyclodextrins in chiral capillary electrophoresis

et al. 2008

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The members of the enantiomeric pairs frequently show rather different biological effects, so their chiral selective synthesis, pharmacological studies and analysis are necessary. CE has unique advantages in chiral analysis. The most frequently used chiral selectors are CDs in this field. This paper gives a short view on the advantages on CE in direct chiral separations, emphasizing the role of CDs. The reason for the broad selectivity spectra of CDs is discussed in detail. The physical background of chiral selective separations is briefly shown in CE. Their interaction mechanisms are shortly defined. The general trend of their use is statistically evaluated. Most frequently used CDs and CD derivatives are characterized. Advantages of ionizable CDs and single-isomer derivatives are shown. The general trend of their use is established.

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“…In CD-modified MEKC the enantioseparation of miconazol improved in the presence of 1 M urea [7]. Using a dual CD system consisting of 5-20 mM b-CD and 20 mM 6-monodeoxy-6-monoamino-b-CD several polychlorinated biphenyl compounds could only be resolved when 2 M urea was added [5]. Furthermore, pH-dependent effects were observed.…”

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confidence: 88%

Effect of urea on analyte complexation by 2,6‐dimethyl‐β‐CD in peptide enantioseparations by CE

Hammitzsch-Wiedemann

Scriba

2009

Electrophoresis

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The aim of the present study was the investigation of the effect of urea on analyte complexation in CD-mediated separations of peptide enantiomers by CE in the pH range of about 2-5. pH-independent complexation and mobility parameters in the absence and presence of 2 M urea were obtained by three-dimensional, non-linear curve fitting of the effective analyte mobility as a function of pH and heptakis-(2,6-di-O-methyl)-beta-CD concentration. Urea led to decreased binding strength of the CD towards the protonated and neutral analyte enantiomers as well as to decreased mobilities of the free analytes. In contrast, mobilities of the fully protonated enantiomer-CD complexes as well as the pK(a) values of the free and complexed analytes increased. The effect of urea on separation efficiency varied with pH and CD concentration. In the case of Ala-Tyr and Ala-Phe, separations improved in the presence of urea at pH 2.2. In contrast, separations were impaired by urea at pH 3.8 and low concentrations of the CD. Decreased separation efficiency was noted for Asp-PheOMe and Glu-PheNH(2) at low CD concentrations when urea was added but separations improved at higher CD concentrations over the entire pH range studied. The effect of urea on analyte complexation appeared to be primarily non-stereoselective. Furthermore, the pH-dependent reversal of the enantiomer migration order observed for Ala-Tyr and Ala-Phe can be rationalized by the complexation and mobility parameters.

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Comparison of charged cyclodextrin derivatives for the chiral separation of atropisomeric polychlorinated biphenyls by capillary electrophoresis

Cited by 21 publications

References 42 publications

Chiral analysis of pollutants and their metabolites by capillary electromigration methods

Chiral analysis of pollutants and their metabolites by capillary electromigration methods

The role of cyclodextrins in chiral capillary electrophoresis

Effect of urea on analyte complexation by 2,6‐dimethyl‐β‐CD in peptide enantioseparations by CE

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