On‐line two‐dimensional <scp>LC</scp>: A rapid and efficient method for the determination of enantiomeric excess in reaction mixtures

Liu, Qi; Jiang, Xinyu; Zheng, Haixing; Su, Wen; Chen, Xiaoqing; Ye, Hua

doi:10.1002/jssc.201300412

Cited by 9 publications

(3 citation statements)

References 32 publications

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“…Achiral–chiral two-dimensional chromatographic analysis has been known for decades; for example, enantioselective bioanalysis from the 1980s often employed column switching, where serum proteins or other interfering components are removed by a first-dimension separation, with a heart cut of the desired component of interest passing to a second-dimension separation employing a chiral stationary phase (CSP) column. , Modern 2D chromatography experiments have often investigated chiral–achiral or achiral–chiral column configurations, ,− but, except for applications where only a single peak is transferred to the second dimension, it has become something of an axiom that chiral chromatography is too slow for use as a second dimension in comprehensive 2D chromatography. ,− Consequently, the use of chiral separations as the second dimension in comprehensive two-dimensional liquid chromatography (2D-LC) experiments is scarce and limited to readily resolved enantiomeric mixtures. ,, While it is possible to address this issue using peak storage in loops for subsequent analysis, such solutions are slow, in addition to being technically complex. Another alternative is the use of supercritical fluid chromatography (SFC) in the second dimension − in order to speed up chiral separations.…”

mentioning

confidence: 99%

Ultrafast Chiral Chromatography as the Second Dimension in Two-Dimensional Liquid Chromatography Experiments

Barhate

Regalado²,

Contrella³

et al. 2017

Anal. Chem.

109

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Chromatographic separation and analysis of complex mixtures of closely related species is one of the most challenging tasks in modern pharmaceutical analysis. In recent years, two-dimensional liquid chromatography (2D-LC) has become a valuable tool for improving peak capacity and selectivity. However, the relatively slow speed of chiral separations has limited the use of chiral stationary phases (CSPs) as the second dimension in 2D-LC, especially in the comprehensive mode. Realizing that the recent revolution in the field of ultrafast enantioselective chromatography could now provide significantly faster separations, we herein report an investigation into the use of ultrafast chiral chromatography as a second dimension for 2D chromatographic separations. In this study, excellent selectivity, peak shape, and repeatability were achieved by combining achiral and chiral narrow-bore columns (2.1 mm × 100 mm and 2.1 mm × 150 mm, sub-2 and 3 μm) in the first dimension with 4.6 mm × 30 mm and 4.6 mm × 50 mm columns packed with highly efficient chiral selectors (sub-2 μm fully porous and 2.7 μm fused-core particles) in the second dimension, together with the use of 0.1% phosphoric acid/acetonitrile eluents in both dimensions. Multiple achiral × chiral and chiral × chiral 2D-LC examples (single and multiple heart-cutting, high-resolution sampling, and comprehensive) using ultrafast chiral chromatography in the second dimension are successfully applied to the separation and analysis of complex mixtures of closely related pharmaceuticals and synthetic intermediates, including chiral and achiral drugs and metabolites, constitutional isomers, stereoisomers, and organohalogenated species.

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mentioning

confidence: 99%

Ultrafast Chiral Chromatography as the Second Dimension in Two-Dimensional Liquid Chromatography Experiments

Barhate

Regalado²,

Contrella³

et al. 2017

Anal. Chem.

109

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“…Liu et al. had compared Chiralcel OD‐H, OJ‐H, AS‐H, and AD‐H columns for the separation of the enantiomers of 2‐phenyl‐2,3‐dihydro‐4‐quinolone (Fig. ).…”

Section: Chiral Resolution By Hplcmentioning

confidence: 99%

Chiral separation of quinolones by liquid chromatography and capillary electrophoresis

2017

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The quinolones are derivatives of oxoquinolines and mostly known for their antibacterial and antiviral activities. Many quinolones are chiral compounds having asymmetric centers and important due to their enantioselective biological activities. In order to study the biological activities of quinolone enantiomers, to control the manufacturing of homochiral drugs and to prepare necessary quantities of pure enantiomers for preclinical or clinical trials, respective chiral separation methods are urgently needed. In this context, the present review discusses chromatographic and electrophoretic methods for the enantioseparation of chiral quinolones and provides some useful information on their physical and pharmaceutical properties. The drawbacks of currently used techniques are revealed and ways to overcome them are outlined. Moreover, recommendations for an optimal choice of a separation protocol are given.

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“…As far as we know, due to the limited peak capacity of 1D‐LC, identifying co‐eluted or structurally similar compounds with similar fragments increasingly relies on 2D‐LC . 2D‐LC using different separation materials could improve separation selectivity and resolution, and facilitate the analysis of much more components in natural resources . Based on whether the components could be eluted from the first dimension into the second dimension directly or not, this method could be performed either with on‐line or off‐line mode .…”

Section: Introductionmentioning

confidence: 99%

Screening and identifying antioxidants from Oplopanax elatus using 2,2ʹ‐diphenyl‐1‐picrylhydrazyl with off‐line two‐dimensional HPLC coupled with diode array detection and tandem time‐of‐flight mass spectrometry

Shao

Nie

Chen

et al. 2016

J of Separation Science

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The root of Oplopanax elatus (Nakai) Nakai has a well-known history of use for the treatment of diseases such as neurasthenia, cardiovascular disorders, and cancer by the native people in northeast China. It is important to screen and identify the bioactive molecules from its root rapidly. Hereby, an off-line two-dimensional high performance liquid chromatography coupled with diode array detection and tandem time-of-flight mass spectrometry together with 2,2'-diphenyl-1-picrylhydrazyl was established to screen antioxidants from the root of O. elatus. A Waters cyanogen column (150 × 3.9 mm, id, 4 μm) was used for the first dimensional liquid chromatography, while a Hypersil BDS-C18 column (250 × 4.6 mm, id, 5 μm) was installed for the second dimension liquid chromatographic analysis. Twenty-eight compounds had been tentatively identified from the methanol extract of the air-dried root of O. elatus including six polyynes and eight phenolic derivatives were screened with antioxidant activity. The developed method could be expedient for screening and identifying antioxidants from O. elatus.

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On‐line two‐dimensional LC: A rapid and efficient method for the determination of enantiomeric excess in reaction mixtures

Cited by 9 publications

References 32 publications

Ultrafast Chiral Chromatography as the Second Dimension in Two-Dimensional Liquid Chromatography Experiments

Ultrafast Chiral Chromatography as the Second Dimension in Two-Dimensional Liquid Chromatography Experiments

Chiral separation of quinolones by liquid chromatography and capillary electrophoresis

Screening and identifying antioxidants from Oplopanax elatus using 2,2ʹ‐diphenyl‐1‐picrylhydrazyl with off‐line two‐dimensional HPLC coupled with diode array detection and tandem time‐of‐flight mass spectrometry

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