Preparation and evaluation of a novel N-benzyl-phenethylamino-β-cyclodextrin-bonded chiral stationary phase for HPLC

Li, Liang; Cheng, Biaoping; Ren-Dan, Zhou; Cao, Zhigang; Zeng, Chun; Li, Laisheng

doi:10.1016/j.talanta.2017.06.009

Cited by 51 publications

(23 citation statements)

References 26 publications

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“…With addition of TEA, retention time of basic analytes was decreased, the peaks became symmetrical, and resolution of the enantiomers was also improved. Retention and enantioselectivity on cyclodextrin CSP can be fine tuned by adjusting the ratio of HOAc and TEA in mobile phase, mostly in polar organic mode . Potential effects from both, acidic and basic additives with cyclodextrin CSPs were few investigated in the normal phase mode .…”

Section: Resultsmentioning

confidence: 99%

A new single‐urea‐bound 3,5‐dimethylphenylcarbamoylated β‐cyclodextrin chiral stationary phase and its enhanced separation performance in normal‐phase liquid chromatography

et al. 2017

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A new single-urea-bound chiral stationary phase based on 3,5-dimethylphenylcarbamoylated β-cyclodextrin was prepared through the Staudinger reaction of mono (6 -azido-6 -deoxy)-per(3,5-dimethylphenylcarbamoylated) β-cyclodextrin and 3-aminopropyl silica gel under CO atmosphere. The new phase exhibited good enantioseparation performance for 33 analytes using normal-phase HPLC conditions; 19 of them were baseline separated. Effects of structure of analytes, alcoholic modifiers, and acidic/basic additives on separation performances of this new cyclodextrin chiral stationary phase have been studied in detail. The results showed that the retention and resolution of acidic and basic analytes on the CSP were greatly affected by the additives. Peak symmetry for some analytes could be improved by simultaneously adding acidic and basic additives to the mobile phase. This work expands the potential applications of the cyclodextrin-based chiral stationary phases in the normal-phase HPLC.

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Section: Resultsmentioning

confidence: 99%

A new single‐urea‐bound 3,5‐dimethylphenylcarbamoylated β‐cyclodextrin chiral stationary phase and its enhanced separation performance in normal‐phase liquid chromatography

et al. 2017

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“…It is well known that enantiomers of a chiral drug compound can produce different potencies, toxicity, and behavior in biological systems . Development of new chiral stationary phases (CSPs) possessing high enantioselectivity for efficient chiral separations of chiral drug compounds is still an active and important field in HPLC . Due to the special spatial structure and properties of native β‐cyclodextrin (β‐CD) and its derivatives, the β‐CD‐based CSPs play important roles in the separation of chiral drugs .…”

Section: Introductionmentioning

confidence: 99%

Preparation and evaluation of partially‐substituted 3‐chloro‐4‐methylphenylcarbamate‐β‐cyclodextrin bonded silica particles as chiral stationary phase for multi‐mode HPLC

Meng

et al. 2019

Separation Science Plus

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3‐Chloro‐4‐methylphenylcarbamate‐(3‐(2‐O‐β‐cyclodextrin)‐2‐hydroxypropoxy)‐propylsilyl‐appended silica particles (CMP‐CD‐HPS), a new type of partially‐substituted cyclodextrin‐bonded phase, have been successfully synthesized and applied as a chiral stationary phase in high‐performance liquid chromatography under multi‐mode conditions including normal phase, reversed phase, and polar organic mobile phase conditions. Chemical characterization for the CMP‐CD‐HPS was carried out by elemental analysis. The chromatographic performance of CMP‐CD‐HPS‐packed column was evaluated by separating the positional isomers of nitrophenol and nitraniline and the enantiomers of some chiral drug compounds. The separation results show that CMP‐CD‐HPS exhibited excellent selectivity for separating the positional isomers of disubstituted benzenes and the enantiomers of the chiral drugs. The hydroxyl residues of partially‐substituted β‐cyclodextrin and the stable spacer linking to secondary hydroxyl site of the β‐cyclodextrin in the new CMP‐CD‐HPS phase play important roles in the chromatographic separations.

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“…Techniques including chromatography and capillary electrophoresis have been developed for the analysis of chiral compounds . HPLC with chiral stationary phases is far and away the most powerful and widely used technique for solvent‐based enantiomeric separations at both analytical and preparative scales.…”

Section: Introductionmentioning

confidence: 99%

Quantification of enantiomers by mass spectrometry based on chemical derivatization and spectral shape deformation quantitative theory

et al. 2019

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A facile mass spectrometric kinetic method for quantitative analysis of chiral compounds was developed by integrating mass spectrometry based on chemical derivatization and the spectral shape deformation quantitative theory. Chemical derivatization was employed to introduce diastereomeric environments to the chiral compounds of interest, resulting in different abundance distribution patterns of fragment ions of the derivatization products of enantiomers in mass spectrometry.The quantitative information of the chiral compounds of interest was extracted from complex mass spectral data by an advanced calibration model derived based on the spectral shape deformation quantitative theory. The performance of the proposed method was tested on the quantitative analysis of R-propranolol in propranolol tablets. Experimental results demonstrated that it could achieve accurate and precise concentration ratio predictions for R-propranolol with an average relative predictive error (ARPE) of about 4%, considerably better than the corresponding results of the mass spectrometric method based on chemical derivatization and the univariate ratiometric model (ARPE: about 12%). The limit of detection (LOD) and limit of quantification (LOQ) of the proposed method for the concentration ratio of R-propranolol were estimated to be 1.5% and 6.0%, respectively. The proposed method is complementary to the existing methods designed for the quantification of enantiomers such as the Cooks kinetic method.

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Preparation and evaluation of a novel N-benzyl-phenethylamino-β-cyclodextrin-bonded chiral stationary phase for HPLC

Cited by 51 publications

References 26 publications

A new single‐urea‐bound 3,5‐dimethylphenylcarbamoylated β‐cyclodextrin chiral stationary phase and its enhanced separation performance in normal‐phase liquid chromatography

A new single‐urea‐bound 3,5‐dimethylphenylcarbamoylated β‐cyclodextrin chiral stationary phase and its enhanced separation performance in normal‐phase liquid chromatography

Preparation and evaluation of partially‐substituted 3‐chloro‐4‐methylphenylcarbamate‐β‐cyclodextrin bonded silica particles as chiral stationary phase for multi‐mode HPLC

Quantification of enantiomers by mass spectrometry based on chemical derivatization and spectral shape deformation quantitative theory

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