Enantioseparation of (RS)-ibuprofen by closed recycling high-speed counter-current chromatography using hydroxypropyl-β-cyclodextrin as chiral selector

Rong, Liya; Liu, Qi; Wang, Jun; Zeng, Hualiang; Ye, Hua; Chen, Xiaoqing

doi:10.1016/j.tetasy.2016.03.001

Cited by 25 publications

(19 citation statements)

References 33 publications

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“…However, only very limited numbers 682 QIU ET AL. Thus, numerous novel strategies were used to improve the separation efficiency for enantioseparation by CCC, including modification of chiral selector [21,22], recycling elution mode [23,24] and biphasic recognition [25,26]. The number of theoretical plates of the separation column of CCC being much lower than that of conventional LC makes it difficult to be successfully applied in enantioseparations.…”

Section: Introductionmentioning

confidence: 99%

“…F I G U R E 1 Stereochemical structures of acetyltropic acid enantiomer of studies are available, which are about enantioseparations by CCC [16][17][18][19][20]. To the best of our knowledge, only two papers have been published so far with regard to enantioseparation by CCC using sulfobutyl ether-β-cyclodextrin as chiral selector [26,27], although many papers have been published for enantioseparation by liquid-liquid partition chromatography using hydroxypropyl-β-cyclodextrin and other substituted β-cyclodextrin as chiral selectors [16][17][18][19][20][22][23][24]. At the same time, it is difficult to find a biphasic solvent system along with a chiral selector showing high enantiorecognition toward enantiomer, in which the chiral selector should be predominantly dissolved in only one phase of the biphasic solvent system while the racemate to be enantioseparated can partition freely in both phases.…”

Section: Introductionmentioning

confidence: 99%

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Enantioseparation of acetyltropic acid by countercurrent chromatography with sulfobutyl ether‐β‐cyclodextrin as chiral selector

Qiu

Sun

Wang

et al. 2019

J of Separation Science

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Acetyltropic acid is an important synthetic intermediate for preparation of tropane alkaloid derivatives, which can be used as anticholinergic drugs, deliriants, and stimulants. In the present work, acetyltropic acid was successfully enantioseparated by countercurrent chromatography using sulfobutyl ether-β-cyclodextrin as chiral selector. A biphasic solvent system composed of n-butyl acetate/n-hexane/0.1 mol/L citrate buffer at pH = 2.2 containing 0.1 mol/L of sulfobutyl ether-β-cyclodextrin (7:3:10, v/v) was selected, which produced a suitable distribution ratio D S = 1.14, D R = 2.31 and a high enantioseparation factor α = 2.03. Baseline separation was achieved for preparative enantioseparation of 50 mg of racemic acetyltropic acid. A method for chiral analysis of acetyltropic acid by conventional reverse phase liquid chromatography with hydroxylpropyl-β-cyclodextrin as mobile phase additive was established, and formation constants of inclusion complex were determined. It was found that different substituted β-cyclodextrin should be selected for enantioseparation of acetyltropic acid by countercurrent chromatography and reverse phase liquid chromatography. K E Y W O R D Sacetyltropic acid, countercurrent chromatography, cyclodextrins, enantioseparation, liquid chromatography J Sep Sci 2020;43:681-688.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Enantioseparation of acetyltropic acid by countercurrent chromatography with sulfobutyl ether‐β‐cyclodextrin as chiral selector

Qiu

Sun

Wang

et al. 2019

J of Separation Science

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“…Rong et al. resolved the enantiomers of ibuprofen using HSCCC column with a two‐phase solvent system composed of n ‐hexane/ethyl acetate/phosphate buffer solution containing 0.1 mol/L hydroxypropyl‐β‐cyclodextrin. However, more efforts should be made on HSCCC separation of enantiomers to seek for a more applicable rule on choosing a suitable solvent system.…”

Section: Introductionmentioning

confidence: 99%

“…Tong et al [25,26] resolved the enantiomers of naproxen and epimeric aromatic acid (-)-menthol esters using preparative HSCCC column with hydroxypropyl-β-cyclodextrin as chiral selector. Rong et al [27] resolved the enantiomers of ibuprofen using HSCCC column with a two-phase solvent system composed of n-hexane/ethyl acetate/phosphate buffer solution containing 0.1 mol/L hydroxypropyl-β-cyclodextrin. However, more efforts should be made on HSCCC separation of enantiomers to seek for a more applicable rule on choosing a suitable solvent system.…”

Section: Introductionmentioning

confidence: 99%

Enantioseparation of pheniramine enantiomers by high‐speed countercurrent chromatography using β‐cyclodextrin derivatives as a chiral selector

Wang

Xie

et al. 2017

J of Separation Science

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The enantioselective separation of pheniramine was studied by a high-speed countercurrent chromatography method using β-cyclodextrin derivatives as a chiral selector. Several key variables, for instance, type of organic solvent and chiral selector, concentration of chiral selector, pH value of aqueous phase, and temperature on the enantioselectivity, were investigated systematically by liquid-liquid extraction experiments. Combining the results of extraction experiments and high-speed countercurrent chromatography, the most suitable conditions for separation of pheniramine enantiomers were obtained with the two-phase system that consisted of isobutyl acetate/aqueous phase, containing 0.02 mol/L carboxymethyl-β-cyclodextrin, pH 8.50 at 278.15 K. Under the optimal conditions, pheniramine enantiomer was successfully resolved after four cycles of high-speed countercurrent chromatography. By using high-performance liquid chromatography to analyze the fractions, the purities of both (+)-pheniramine and (-)-pheniramine were over 99% and the recovery of this method was up to 85-90%.

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“…There are many published methods regarding ibuprofen chiral resolution, mainly made by chromatographic methods [3][4][5][6][7][8][9][10][11] and few by capillary electrophoresis [12][13][14][15][16]. In general, the methods are designed to analyze enantiomers in biological environment for different purposes such as enantiomers conversion, differences regarding their biological behavior etc.…”

Section: Introductionmentioning

confidence: 99%

Research Article. The Influence of Some Parameters on Chiral Separation of Ibuprofen by High-Performance Liquid Chromatography and Capillary Electrophoresis

Balint

Cârje

Muntean

et al. 2017

Acta Medica Marisiensis

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Objective: The aim of the study was to compare the influence of mobile phase composition and temperature on chiral separation of racemic ibuprofen by capillary electrophoresis and high performance liquid chromatography with UV detection. Materials and methods: Racemic ibuprofen was analysed on a chiral OVM column with an HPLC system 1100 Agilent Technologies, under isocratic elution, by using potassium dihydrogen phosphate 20 mM and ethanol in mobile phase. The flow rate was set at 1 mL/min, UV detector at 220 nm and different column temperatures were tested. For electrophoresis separation an Agilent CE G1600AX Capillary Electrophoresis System system, with UV detection, was used. The electrophoresis analysis was performed at different pH values and temperatures, with phosphate buffer 25 mM and methyl-β-cyclodextrin as chiral selector. Results: The chromatograhic analysis reveals a high influence of mobile phase pH on ibuprofen enantiomers separation. An elution with a mixture of potassium dihydrogen phosphate 20 mM pH=3 and ethanol, at 25ºC, allowed enantiomers separation with good resolution in less than 8 min. Conclusions: The proposed HPLC method proved suitable for the separation of ibuprofen enantiomers with a good resolution, but the capillary electrophoresis tested parameters did not allow chiral discrimination.

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Enantioseparation of (RS)-ibuprofen by closed recycling high-speed counter-current chromatography using hydroxypropyl-β-cyclodextrin as chiral selector

Cited by 25 publications

References 33 publications

Enantioseparation of acetyltropic acid by countercurrent chromatography with sulfobutyl ether‐β‐cyclodextrin as chiral selector

Enantioseparation of acetyltropic acid by countercurrent chromatography with sulfobutyl ether‐β‐cyclodextrin as chiral selector

Enantioseparation of pheniramine enantiomers by high‐speed countercurrent chromatography using β‐cyclodextrin derivatives as a chiral selector

Research Article. The Influence of Some Parameters on Chiral Separation of Ibuprofen by High-Performance Liquid Chromatography and Capillary Electrophoresis

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