Free solution capillary electrophoresis and micellar electrokinetic resolution of amino acid enantiomers and peptide isomers with L- and D-Marfey's reagents

Tran, An D.; Blanc, Timothy; Leoplod, Eric J.

doi:10.1016/s0021-9673(01)90222-5

Cited by 107 publications

(30 citation statements)

References 7 publications

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“…In one of the first papers on the topic Tran, Blanc and Leoplod described the separation of amino acid enantiomers with high-performance capillary electrophoresis (HPCE), after derivatization with Marfey's reagent (1-Fluoro-2,4 dinitrophenyl-5-L-alanine amide, FDAA) [4]. Since then, capillary electrophoresis has been widely applied in routine analysis and also a number of reviews have been published [1]- [5].…”

Section: Introductionmentioning

confidence: 99%

Capillary Electrophoresis in Determination of Low Molecular Mass Organic Acids

Wasielewska¹,

Banel²,

Zygmunt³

2014

IJESD

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Abstract-This paper presents overviews the capabilities of capillary electrophoretic techniques to determine low molecular mass organic acids in a variety of aqueous, gas and solid samples. It mainly focuses on short -chain carboxylic acids containing one or more carboxylic groups and possibly some other functional groups (hydroxyl, keto-, amino-etc.). Finally the procedures applied to the determine the acids in different matrices are shortly characterized.The principles of capillary electrophoresis its advantages over gas and liquid chromatographic separation and detection modes are briefly discussed. Finally, the brief overview of the technique is followed by characterization of CE based procedures for the analysis of a variety of samples such as food, environmental, biological etc. for the content of organic acids, mainly those with carboxylic groups.Index Terms-Capillary electrophoresis, low molecular mass organic acids.

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Section: Introductionmentioning

confidence: 99%

Capillary Electrophoresis in Determination of Low Molecular Mass Organic Acids

Wasielewska¹,

Banel²,

Zygmunt³

2014

IJESD

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“…Precolumn derivatization often improves the detection sensitivity as well [3]. To date, an array of chiral derivatizing reagents including Marfey's reagent [4], 2,3,4,6-tetra-O-acetyl-b-D-glucopyranosylisothiocyanate [5], (1)-or (2)-1-(9-fluorenyl)ethyl chloroformate [6]…”

Section: Introductionmentioning

confidence: 99%

Degradingdehydroabietylisothiocyanate as a chiral derivatizing reagent for enantiomeric separations by capillary electrophoresis

et al. 2006

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Abietic acid is a naturally occurring enantiomeric diterpenic acid. Its absolute optical purity and very stable stereochemistry structure makes it an excellent starting material for preparing chiral derivatizing reagents for chromatographic or electrophoretic applications. This paper describes the synthesis and evaluation of a novel chiral derivatization reagent, i.e., degradingdehydroabietylisothiocyanate (DDHAIC) derived from dehydroabietic acid. Its applicability for the enantioseparation of racemic amino acids by CE was demonstrated. DDHAIC reacted readily with amino acids at an elevated temperature (70 degrees C). The resulting derivatives were highly stable and separable by MEKC. Separation of amino acid-DDHAIC diastereomers was achieved with a running buffer consisting of 50 mM Na(2)HPO(4) (pH 9.0), 18 mM SDS, and 25% v/v ACN. Under the conditions selected, diastereomers formed from ten pairs of tested amino acid enantiomers including D/L-Asn, D/L-Met, D/L-Leu, D/L-Phe, D/L-Trp, D/L-Ser, D/L-Val, D/L-Ala, D/L-Thr, and R/S-vigabatrin were well resolved. The resolution values were in the range of 0.95-8.9.

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“…[9,10,[24][25][26][27][28][29][30][31][32]. Since the electrophoretic mobilities of the diastereomeric derivatives are different, the derivatives can be separated by their own electrophoretic mobilities in an achiral separation environment.…”

Section: Introductionmentioning

confidence: 99%

“…A requirement for successful application of the indirect method is that the purity of the chiral reagent used for the derivatization must be high, or the concentration of the impurity must be known for a correction [24]. Further, it is desirable that the derivatization reaction is rapid, simple, and can be performed at room temperature to avoid racemization.To date, various chiral reagents have been used for the formation of diastereomers of amino acids for subsequent CE separation [10,[25][26][27][28][29][30][31][32] …”

mentioning

confidence: 99%

Precolumn diastereomerization and micellar electrokinetic chromatography on a plastic microchip: Rapid chiral analysis of amino acids

Hahn

2005

Electrophoresis

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Precolumn derivatization and chiral separation of DL-amino acids based on diastereomerization have been performed on an integrated poly(dimethylsiloxane) microchip. Diastereomeric derivatives were formed in a microfabricated precolumn reactor by the reaction of amino acid enantiomers with o-phthaldialdehyde/2,3,4,6-tetra-O-acetyl-1-thio-beta-D-glucopyranose (OPA/TATG), and separated by MEKC in an achiral environment without chiral selectors in the running buffer. Optimized precolumn reactions and chiral separations of amino acids were achieved within 2.5 min. Resolutions of diastereomers of OPA/TATG-amino acids were in the range of 2.5-6.1 at optimized separation conditions. Simultaneous separation of a mixture of five chiral amino acids was successfully performed in a single run in less than 100 s.

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Free solution capillary electrophoresis and micellar electrokinetic resolution of amino acid enantiomers and peptide isomers with L- and D-Marfey's reagents

Cited by 107 publications

References 7 publications

Capillary Electrophoresis in Determination of Low Molecular Mass Organic Acids

Capillary Electrophoresis in Determination of Low Molecular Mass Organic Acids

Degradingdehydroabietylisothiocyanate as a chiral derivatizing reagent for enantiomeric separations by capillary electrophoresis

Precolumn diastereomerization and micellar electrokinetic chromatography on a plastic microchip: Rapid chiral analysis of amino acids

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