Electrochromatographic Enantioseparation of Amino Acids Using Polybutylmethacrylate‐based Chiral Monolithic Column by Capillary Electrochromatography

Abstract

This article describes the development of a polybutylmethacrylate-based monolithic capillary column as a chiral stationary phase. The chiral monolithic column was prepared by polymerization of butyl methacrylate (BMA), ethylene dimethacrylate (EDMA), and N-methacryloyl-L-glutamic acid (MAGA) in the presence of porogens. The porogen mixture included N,N-dimethyl formamide and phosphate buffer. MAGA was used as a chiral selector. The effect of MAGA content was investigated on electrochromatographic enantioseparation of D,L-histidine, D,L-tyrosine, D,L-phenyl alanine, and D,L-glutamic acid. The effect of acetonitrile (ACN) content in mobile phase on electro-osmotic flow was also investigated. It was demonstrated that the poly(BMA-EDMA-MAGA) monolithic chiral column can be used for the electrochromatographic enantioseparation of amino acids by capillary electrochromatography (CEC). The mobile phase was ACN/10 mM phosphate buffer (45:55%) adjusted to pH 2.7. It was observed that L-enantiomers of the amino acids migrated before D-enantiomers. The separation mechanism of electrochromatographic enantioseparation of amino acids in CEC is discussed.

Enantioseparation of aromatic amino acids using CEC monolith with novel chiral selector, N‐methacryloyl‐l‐histidine methyl ester

“…As can be also seen from Fig. , since increase of the pH results in increasing EOF and the enantiomer with high affinity to the chiral selector migrated slower than the one having less affinity to the chiral selector and consequently, the reversal of EMO for d , l ‐tryptophan was observed. At the same time, the reversal of EMO types of the pH‐dependent were also shown in the literature .…”

“…It was observed that l ‐enantiomers of the solute migrated before d ‐enantiomers. The reason of this result was explained by our previous work . The molecular interactions between chiral stationary phase and analytes were based on different stereostructures.…”

Chiral Separations by Capillary Electrophoresis and related Techniques with Different Chiral Selectors: A Review

“…Since there is no pressure drop across the column in CEC, it is possible to use the columns. However, the main difference between LC and CEC is the use of functional monomers such as 2-acrylo amido, 2-methyl propane sulfonic acid (AMPS), N-Methacryloyl-L-phenylalanine (MAPA), which can provide electroosmotic flow [24,25].…”

Organic polymer‐based monolithic capillary columns and their applications in food analysisψ

“…These types of monoliths are usually used for the enantioseparation of chiral drugs. Even though the enantioseparation of AAs could be well achieved using a chiral monomer in the preparation of chiral PMCs [64,65], AA based imprinted chiral PMCs have also been prepared and applied for the enantioseparation of AAs [66,67]. The preparation and evaluation of the imprinted PMC as a molecular imprinted SPE (MISPE) for the determination of auramine O in shrimp was reported by Li et al [68].The column was prepared by in-situ polymerization of MAA as the main monomer and EDMA as the crosslinker.…”