Chiral separations in capillary electrophoresis

Vespalec, Radim; Boček, Petr

doi:10.1002/(sici)1522-2683(19990901)20:13<2579::aid-elps2579>3.0.co;2-r

Cited by 86 publications

(14 citation statements)

References 209 publications

(221 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In contrast, since enantiomers have identical behavior under chromatographic conditions, conventional GC/MS requires specific enantiomer derivatization to diastereoisomers, that are chromatographically distinguishable. On the other hand, GC/MS provides a sensitivity that is difficult to reach by CE methods, although some strategies to decrease limits of detection have been developed for electrophoresis 32,33. With regard to HPLC, enantiomers of amphetamine‐like compounds are usually separated with the use of specific chiral columns, resulting in a substantial increase in cost.…”

Section: Resultsmentioning

confidence: 99%

Stereochemical analysis of 3,4‐methylenedioxymethamphetamine and its main metabolites by gas chromatography/mass spectrometry

Pizarro

Llebaría

Cano

et al. 2003

Rapid Comm Mass Spectrometry

View full text Add to dashboard Cite

3,4-Methylenedioxymethamphetamine (MDMA, ecstasy) is consumed as the racemate but some metabolic steps are enantioselective. In addition, chiral properties are preserved during MDMA biotransformation. A quantitative analytical methodology using gas chromatography/mass spectrometry (GC/MS) to determine enantioselective disposition in the body of MDMA and its main metabolites including 3,4-methylenedioxyamphetamine (MDA), 4-hydroxy-3-methoxymethamphetamine (HMMA), and 4-hydroxy-3-methoxyamphetamine (HMA) was developed. Plasma and urine samples were collected from a male volunteer. The analysis of MDMA, MDA, and 4-hydroxy-3-methoxy metabolites by GC/MS required a two-step derivatization procedure. The first step consisted of derivatization of the amine with enantiomerically pure Mosher's reagent ((R)-MTPCl). Triethylamine was used as a base to neutralize hydrochloric acid formed during the reaction allowing quantitative derivatization, which resulted in a substantial improvement in the sensitivity of the method compared with other previously described techniques. Further treatment with ammonium hydroxide was required since both amine and hydroxyl groups underwent derivatization in the reaction. Ammonium hydroxide breaks bonds formed with hydroxyl groups without affecting amine derivatives. The second derivatization step using hexamethyldisilazane was needed for metabolites containing phenol residues. This derivatization method permitted the stereochemically specific study of MDMA and its main monohydroxylated metabolites by GC/MS. A detailed study of the chemical reactions involved in the derivatization steps was indispensable to develop a straightforward, sensitive, and reproducible method for the analysis of the parent drug compound and its metabolites.

show abstract

Section: Resultsmentioning

confidence: 99%

Stereochemical analysis of 3,4‐methylenedioxymethamphetamine and its main metabolites by gas chromatography/mass spectrometry

Pizarro

Llebaría

Cano

et al. 2003

Rapid Comm Mass Spectrometry

View full text Add to dashboard Cite

show abstract

“…Contrarily, direct resolution is achieved by using chiral selectors in BGE. The theoretical consideration of chiral recognition mechanisms in CE was reviewed by Vespalec and Bocek [36]. In case of cyclodextrins, the inclusion diastereomeric complexes are formed which are controlled by a number of interactions such ascomplexation, hydrogen bonding, dipole-dipole interactions, ionic bindings and steric affects.…”

Section: Mechanisms Of Chiral Resolutionmentioning

confidence: 99%

Chiral Analyses of Pollutants by Capillary Electrophoresis

Ali¹

2010

TOCBMJ

View full text Add to dashboard Cite

Abstract:The determination of enantiomeric composition of chiral xenobiotics and pollutants is a very difficult job due to their low amounts and poor detection by commonly used UV detector. But this sort of analysis is an important issue from the health point of view. The chiral analyses of these notorious pollutants by capillary electrophoresis have been discussed in this article. This review discusses the new trends and advancements, which have been achieved in the analyses of chiral pollutants using capillary electrophoresis and the state-of-art of their enaniomeric resolution. This article focuses on sample treatment, applications, optimization, detection, mechanisms of chiral resolution and future perspectives of CE in chiral resolution of xenobiotics. Besides, efforts have also been made to suggest the improvement in CE machine to make it ideal for the analyses of chiral xenobiotics at trace levels.

show abstract

“…Due to the high efficiency, resolution power, speed and miniaturization, CE techniques have become very popular methods for chiral analysis and stereoisomer separation [205][206][207] including chiral and stereoselective separa- tions of peptides and amino acids [45]. Diastereomeric pairs of dipeptides LD-Ala-LD-Phe and Leu-Phe, i.e., LL+DD pair and LD+DL pair of both peptides have been separated by CZE in 70 mM phosphate buffer, 2 M urea BGE, at pH 3 [208] (see Fig.…”

Section: Chiral Analysis and Stereoisomer Separationmentioning

confidence: 99%

Recent advances in capillary electrophoresis of peptides

Kašička

2001

Electrophoresis

View full text Add to dashboard Cite

The article gives a comprehensive review on the recent developments in the applications of high-performance capillary electromigration methods, including zone electrophoresis, isotachophoresis, isoelectric focusing, affinity electrophoresis, electrokinetic chromatography and electrochromatography, to analysis, preparation and physicochemical characterization of peptides. The article presents new approaches to the theoretical description and experimental verification of electromigration behavior of peptides, and covers the methodological aspects of capillary electroseparations of peptides, such as strategy and rules for the rational selection of separation mode and experimental conditions, sample treatment, suppression of peptide adsorption to the inner capillary wall, new developments in individual separation modes and new designs of detection systems. Several types of applications of capillary electromigration methods to peptide analysis are presented: conventional qualitative and quantitative analysis for determination of purity, determination in biomatrices, monitoring of physical and chemical changes and enzymatic conversions, amino acid and sequence analysis and peptide mapping of proteins. Some examples of micropreparative peptide separations are given and capabilities of capillary electromigration techniques to provide important physicochemical characteristics of peptides are demonstrated.

show abstract

Chiral separations in capillary electrophoresis

Cited by 86 publications

References 209 publications

Stereochemical analysis of 3,4‐methylenedioxymethamphetamine and its main metabolites by gas chromatography/mass spectrometry

Stereochemical analysis of 3,4‐methylenedioxymethamphetamine and its main metabolites by gas chromatography/mass spectrometry

Chiral Analyses of Pollutants by Capillary Electrophoresis

Recent advances in capillary electrophoresis of peptides

Contact Info

Product

Resources

About