Progress of chiral ligand-exchange capillary electrophoresis for enantioseparation

Qi, Li; Qiao, Juan

doi:10.1016/j.chroma.2022.463381

Cited by 10 publications

(10 citation statements)

References 56 publications

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“…[17][18][19][20][21][22][23][24][25] A recent review paper also analyzed and reported chiral ligand exchange capillary electrophoresis (CLE-CE). 126 Most chiral ligands used in the CLE-CE are amino acids or their derivatives except for an amino alcohol, (S)-3-amino-1,2-propanediol. 127 First, covalently bonded ligand exchange CSPs prepared by amino alcohols were reported by Yuki et al 70,71 Two diastereomeric amino alcohols, (1R,2S)-and (1S,2S)-2-amino-1,2-diphenylethanol, were converted to (1R,2S)and (1S,2S)-2-carboxymethylamino-1,2-diphenylethanol by treating them with ethyl bromoacetate and then with 1 M NaOH solution.…”

Section: Amino Alcohol-based Diastereomeric Pirkle-type and Ligand Ex...mentioning

confidence: 99%

“…The structures of C3 symmetric CSPs 45-50. it was revealed that the phenyl group attached to the amide linkage in the chiral selectors is crucial to chiral separation. 121 Diastereomeric chiral compounds, such as the 1,2-diphenylethylenediamine (DPEDA), 20 2-amino-1,2-diphenylethanol (ADPE), 125 and 1,2diaminocyclohexane, 126 have been applied in the field of chiral separation as chiral selectors. Among these diastereomeric CPSs, DPEDA-based CSP was commercialized as "ULMO" and showed impressive chiral resolutions.…”

Section: Amino Alcohol-based Symmetric Cspsmentioning

confidence: 99%

“…Since Davankov et al 36–38 introduced the chiral ligand exchange principle, various ligand exchange CSPs have been developed by dynamically coating or covalently bonding chiral chelating ligands as chiral selectors on the column supporting materials 17–25 . A recent review paper also analyzed and reported chiral ligand exchange capillary electrophoresis (CLE‐CE) 126 . Most chiral ligands used in the CLE‐CE are amino acids or their derivatives except for an amino alcohol, (S)‐3‐amino‐1,2‐propanediol 127 …”

Section: Amino Alcohol‐based Diastereomeric Pirkle‐type and Ligand Ex...mentioning

confidence: 99%

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Amino alcohol‐derived chiral stationary phases

2023

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An updated minireview of chiral stationary phases (CSPs) based on amino alcohols is presented. In this minireview, we focused on amino alcohols as starting materials in preparation of chiral catalysts for asymmetric organic synthesis and CSPs for chiral separations. Among the various CSPs, we summarized the important developments and applications of the amino alcohol‐based Pirkle‐type CSPs, ligand exchange CSPs, α‐amino acid‐derived amino alcohol CSPs, and symmetric CSPs from their first appearance to the present day to propose ideas for the development of new CSPs with improved performance.

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Section: Amino Alcohol-based Diastereomeric Pirkle-type and Ligand Ex...mentioning

confidence: 99%

Section: Amino Alcohol-based Symmetric Cspsmentioning

confidence: 99%

Section: Amino Alcohol‐based Diastereomeric Pirkle‐type and Ligand Ex...mentioning

confidence: 99%

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Amino alcohol‐derived chiral stationary phases

2023

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“…In the chiral ligand exchange mechanism, the enantioselectivity is achieved via the difference between the thermodynamic stability of the ternary complexes formed between analytes, a central metal ion (e.g., Cu(II)) and chiral ligand, often represented by an enantiomerically pure amino acid. Only limited applications of the method are given in the field of pharma analysis [ 76 , 77 ].…”

Section: Recent Advances In the Development Of Ce Analytical Procedur...mentioning

confidence: 99%

New Trends in the Quality Control of Enantiomeric Drugs: Quality by Design-Compliant Development of Chiral Capillary Electrophoresis Methods

et al. 2022

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Capillary electrophoresis (CE) is a potent method for analyzing chiral substances and is commonly used in the enantioseparation and chiral purity control of pharmaceuticals from different matrices. The adoption of Quality by Design (QbD) concepts in analytical method development, optimization and validation is a widespread trend observed in various analytical approaches including chiral CE. The application of Analytical QbD (AQbD) leads to the development of analytical methods based on sound science combined with risk management, and to a well understood process clarifying the influence of method parameters on the analytical output. The Design of Experiments (DoE) method employing chemometric tools is an essential part of QbD-based method development, allowing for the simultaneous evaluation of experimental parameters as well as their interaction. In 2022 the International Council for Harmonization (ICH) released two draft guidelines (ICH Q14 and ICH Q2(R2)) that are intended to encourage more robust analytical procedures. The ICH Q14 guideline intends to harmonize the scientific approaches for analytical procedures’ development, while the Q2(R2) document covers the validation principles for the use of analytical procedures including the recent applications that require multivariate statistical analyses. The aim of this review is to provide an overview of the new prospects for chiral CE method development applied for the enantiomeric purity control of pharmaceuticals using AQbD principles. The review also provides an overview of recent research (2012–2022) on the applicability of CE methods in chiral drug impurity profiling.

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“…Identifying enantiomers with green and efficient methods still faces many challenges to date. First, traditional enantiomeric identification methods (such as chemiluminescence, chromatography, , capillary electrophoresis, colorimetry, etc.) generally have the disadvantages of cumbersome procedures, high cost, poor stability, and so forth.…”

Section: Introductionmentioning

confidence: 99%

Construction of a Chiral Fluorescent Probe for Tryptophan Enantiomers/Ascorbic Acid Identification

Guan

et al. 2023

ACS Appl. Mater. Interfaces

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Chiral recognition of amino acid enantiomers is critical in enhancing drug efficacy, detecting disease markers, and understanding physiological processes. Enantioselective fluorescent identification has gained attention among researchers due to its nontoxicity, easy synthesis, and biocompatibility. In this work, chiral fluorescent carbon dots (CCDs) were produced through a hydrothermal reaction followed by chiral modification. The fluorescent probe, Fe3+-CCDs (F-CCDs), was constructed by complexing Fe3+ with CCDs to differentiate between the enantiomers of tryptophan (Trp) and determine ascorbic acid (AA) through an “on–off–on” response. It is worth noting that l-Trp can greatly enhance the fluorescence of F-CCDs with a blue shift, whereas d-Trp does not have any effect on the fluorescence of F-CCDs. F-CCDs showed a low limit of detection (LOD) for l-Trp and l-AA, with an LOD of 3.98 and 6.28 μM, respectively. The chiral recognition mechanism of tryptophan enantiomers using F-CCDs was proposed based on the interaction force between the enantiomers and F-CCDs, as confirmed by UV–vis absorption spectroscopy and density functional theory calculations. The determination of l-AA by F-CCDs was also confirmed through the binding of l-AA to Fe3+ to release CCDs, as seen in UV–vis absorption spectra and time-resolved fluorescence decays. In addition, AND and OR gates were constructed based on the different responses of CCDs to Fe3+ and Fe3+-CCDs to l-Trp/d-Trp, demonstrating the significance of molecular-level logic gates in drug detection and clinical diagnosis.

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Progress of chiral ligand-exchange capillary electrophoresis for enantioseparation

Cited by 10 publications

References 56 publications

Amino alcohol‐derived chiral stationary phases

Amino alcohol‐derived chiral stationary phases

New Trends in the Quality Control of Enantiomeric Drugs: Quality by Design-Compliant Development of Chiral Capillary Electrophoresis Methods

Construction of a Chiral Fluorescent Probe for Tryptophan Enantiomers/Ascorbic Acid Identification

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