Synthesis and application of amino alcohol-derived chiral ionic liquids, as additives for enantioseparation in capillary electrophoresis

Ma, Xiaofei; Du, Yingxiang; Sun, Xiaodong; Liu, Jie; Huang, Zhifeng

doi:10.1016/j.chroma.2019.04.040

Cited by 39 publications

(18 citation statements)

References 57 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Compared with other drugs in HPLC separation, orphenadrine had the shortest retention time and the highest Δ E values, demonstrating that the complexes formed by orphenadrine and CDMPC were unstable and, thus, possessed lower retention in chromatographic analysis. Besides, we could predict the enantiomers migration order through the negative Δ E values [52,53]. The binding affinity of ( S )‐enantiomers with CSP was stronger than ( R )‐enantiomers for orphenadrine, meclizine, and carbinoxamine.…”

Section: Resultsmentioning

confidence: 99%

Chiral separation and molecular simulation study of six antihistamine agents on a coated cellulose tri‐(3,5‐dimethylphenycarbamate) column (Chiralcel OD‐RH) and its recognition mechanisms

Liu

Wang

et al. 2021

Electrophoresis

View full text Add to dashboard Cite

Enantiomeric separation of six antihistamine agents was first systematically investigated on a cellulose‐based chiral stationary phase (CSP), that is, cellulose tris‐(3,5‐dimethyl phenyl carbamate) (Chiralcel OD‐RH), under the reversed‐phase mode. Orphenadrine, meclizine, terfenadine, dioxopromethazine, and carbinoxamine enantiomers were completely separated under the optimized mobile phase conditions with resolutions of 5.02, 1.93, 1.68, 1.67, and 1.54, respectively. Mequitazine was partially separated with a resolution of 0.77. The influences of type and concentration of buffer salt, the pH of buffer solution, and the type and ratio of organic modifier on the chiral separation were evaluated and optimized. For a better insight into the enantiorecognition mechanisms, molecular docking was carried out via the Autodock software. The lowest binding energy and the optimal conformations of the analytes/CSP complexes were supplied, and the mechanisms of chiral recognition were determined. According to the results, the key interactions for the chiral recognition of these six analytes on CDMPC were π–π interactions, hydrophobic interactions, hydrogen bond interactions, and some special interactions.

show abstract

Section: Resultsmentioning

confidence: 99%

Chiral separation and molecular simulation study of six antihistamine agents on a coated cellulose tri‐(3,5‐dimethylphenycarbamate) column (Chiralcel OD‐RH) and its recognition mechanisms

Liu

Wang

et al. 2021

Electrophoresis

View full text Add to dashboard Cite

show abstract

“…For more information, please see [34,36] quinate (TMA-D -QUI), was designed and applied to establish a synergistic system with maltodextrin for CE enantioseparation by Yang et al [42], significantly improving enantioselectivity. The other case involved the synthesis of three amino alcoholderived chiral ionic liquids, N,N,N-trimethyl-L -valinolbis(trifluoromethanesulfon)imide, N,N-dimethyl-L -prolinolbis(trifluoromethanesulfon)imide, and N,N,N-trimethyl-Lphenylalaninol-bis(trifluoromethanesulfon)imide), and their application for chiral separation when mixed with 2hydroxypropyl-β-cyclodextrin (HP-β-CD) [43]. This optimized synergistic system significantly improved the separation of six drugs.…”

Section: Ionic Liquid As Buffer Additivesmentioning

confidence: 99%

Recent (2018–2020) development in capillary electrophoresis

Gao

Zhong

2021

Anal Bioanal Chem

View full text Add to dashboard Cite

Development of new capillary electrophoresis (CE) methodology and instrumentation, as well as application of CE to solve new problems, remains an active research area because of the attractive features of CE compared to other separation techniques. In this review, we focus on the representative works about sample preconcentration, separation media or capillary coating development, detector construction, and multidimensional separation in CE, which are judiciously selected from the papers published in 2018-2020.

show abstract

“…1 H- 19 F heteronuclear Overhauser spectroscopy data indicated also the inclusion of EtCholNTf2 into the CD cavity. The enhanced enantioselectivity of selectors in combination with CILs was also studied by CE and molecular modeling for HP-β-CD [99] and maltodextrin [100].…”

Section: Structures Of Selector-selectand Complexesmentioning

confidence: 99%

Advances of capillary electrophoresis enantioseparations in pharmaceutical analysis (2017–2020)

2021

View full text Add to dashboard Cite

Capillary electrophoresis is a powerful technique for the analysis of polar chiral compounds and has been widely accepted for analytical enantioseparations of drug compounds in pharmaceuticals and biological media. In addition, many mechanistic studies have been conducted in an attempt to rationalize enantioseparations in combination with spectroscopic and computational techniques. The present review will focus on recent examples of mechanistic aspects and summarize recent applications of stereoselective pharmaceutical and biomedical analysis published between January 2017 and November 2020. Various separation modes including electrokinetic chromatography in combination with several detection modes including laser-induced fluorescence, mass spectrometry and contactless conductivity detection will be discussed. A general trend also observed in other analytical techniques is the application of quality by design principles in method development and optimization.

show abstract

Synthesis and application of amino alcohol-derived chiral ionic liquids, as additives for enantioseparation in capillary electrophoresis

Cited by 39 publications

References 57 publications

Chiral separation and molecular simulation study of six antihistamine agents on a coated cellulose tri‐(3,5‐dimethylphenycarbamate) column (Chiralcel OD‐RH) and its recognition mechanisms

Chiral separation and molecular simulation study of six antihistamine agents on a coated cellulose tri‐(3,5‐dimethylphenycarbamate) column (Chiralcel OD‐RH) and its recognition mechanisms

Recent (2018–2020) development in capillary electrophoresis

Advances of capillary electrophoresis enantioseparations in pharmaceutical analysis (2017–2020)

Contact Info

Product

Resources

About