Preparative enantioseparation of propafenone by counter-current chromatography using di-<i>n</i>
-butyl l-tartrate combined with boric acid as the chiral selector

Tong, Shengqiang; Shen, Mangmang; Zheng, Yi; Chu, Chu; Li, Xing‐Nuo; Yan, Jizhong

doi:10.1002/jssc.201300614

Cited by 8 publications

(3 citation statements)

References 20 publications

(27 reference statements)

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“…33 Dialkyltartrates have ever been used together with boric acid on enantioselective extraction of some b-blockers, 29,34,35 chiral microemulsion electrokinetic chromatography (MEEKC) of some b-blockers and structurally related compounds, 36,37 some b-blockers and b-agonists in nonaqueous capillary electrophoresis (NACE), [38][39][40] and preparative enantioseparation of three b-blockers in counter-current chromatography (CCC). 41,42 As reported in our previous work, the di-n-hexyl-L-tartrateboric acid complex as a chiral mobile phase additive showed good chiral recognition abilities for the enantioseparations of some b-blockers by reversed-phase high performance liquid chromatography (RP-HPLC) with a C 18 column. 43 Di-n-butyl-Ltartrate is a much cheaper and more easily obtained chiral selector.…”

Section: Introductionmentioning

confidence: 69%

Enantioseparations of three amino alcohols using a di-n-butyl-l-tartrate–boric acid complex as the mobile phase additive by reversed-phase high performance liquid chromatography

Wang

Liu

et al. 2014

Anal. Methods

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Three amino alcohols, propranolol, clenbuterol and cycloclenbuterol, were enantioseparated on an achiral column by reversed-phase high performance liquid chromatography (RP-HPLC). A chiral chromatographic system was established based on C 18 -bonded silica gel as the support and a self-prepared di-n-butyl-Ltartrate-boric acid complex as the chiral mobile phase additive. In order to obtain better enantioseparations, the influences of di-n-butyl-L-tartrate and boric acid concentrations, the type, concentration and pH of the buffer, as well as methanol content were extensively investigated. It was found that the mobile phase composition played an important role in improving the enantioseparations and all of the enantiomers could be baseline resolved under the optimized experimental conditions. Three pairs of enantiomers, which could not be separated with only di-n-butyl-L-tartrate, obtained good chiral separations using the complex chiral selector. The primary driving forces responsible for the chiral recognition were assumed to be the ion-pair interaction between the enantiomers and the chiral selector; and the interactions between the ion-pairs above and the stationary phase also played important roles for the chiral separations in RP-HPLC.

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Section: Introductionmentioning

confidence: 69%

Enantioseparations of three amino alcohols using a di-n-butyl-l-tartrate–boric acid complex as the mobile phase additive by reversed-phase high performance liquid chromatography

Wang

Liu

et al. 2014

Anal. Methods

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“…High‐speed counter‐current chromatography (HSCCC) is an improved liquid–liquid chromatographic technique in which the mobile and stationary phases consist of two immiscible liquids or solutions. When applied to enantioseparation, HSCCC can separate a variety of enantiomers by adding a suitable chiral selector (CS) to the two phases using the same HSCCC column . The same HSCCC column can be applied to either analytical or preparative enantioseparations by adjusting the amount of chiral selector used .…”

Section: Introductionmentioning

confidence: 99%

Synergetic mechanism and enantioseparation of aromatic β‐amino acids by biphasic chiral high‐speed counter‐current chromatography

Han

Luo

et al. 2016

J of Separation Science

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A biphasic chiral recognition system based on chiral ligand exchange with Cu(II)-N-n-dodecyl-L-proline and hydroxypropyl-β-cyclodextrin as an additive was developed to enantioseparate aromatic β-amino acids by high-speed counter-current chromatography. The biphasic chiral recognition system was established with an n-butanol/water (1:1, v/v) solvent system by adding N-n-dodecyl-L-proline and Cu(II) ions to the organic phase and hydroxypropyl-β-cyclodextrin to the aqueous phase. Several separation parameters, such as temperature, pH value, and chiral selector concentration, were systematically investigated by enantioselective liquid-liquid extraction. Under the optimal separation conditions, 54.5 mg of (R,S)-β-phenylalanine and 74.3 mg of (R,S)-β-3,4-dimethoxyphenylalanine were baseline enantioseparated. More importantly, the synergistic enantiorecognition mechanism, based on the Cu(II)-N-n-dodecyl-L-proline and hydroxypropyl-β-cyclodextrin, was discussed for the first time.

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“…Typically, this separation technique is based on the partition of analytes between two immiscible organic–aqueous two‐phase solvent systems without solid support and irreversible adsorption. HSCCC is a essentially form of liquid–liquid partition chromatography in which one of liquid phase of the immiscible two‐phase system is retained in the column as stationary phase with the aid of gravity or a centrifugal force field while the other liquid phase is used as mobile phase . However, most two‐phase solvent systems are limited to separate constituents with a narrow range of polarity, and in fact, plant extracts usually contain very complicated constituents with a broad range of polarity.…”

Section: Introductionmentioning

confidence: 99%

Three-phase solvent systems for the comprehensive separation of a wide variety of compounds fromDicranostigma leptopodumby high-speed counter-current chromatography

et al. 2015

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A three-phase solvent system was efficiently applied for high-speed counter-current chromatography to separate secondary metabolites with a wide range of hydrophobicity in Dicranostigma leptopodum. The three-phase solvent system of n-hexane/methyl tert-butyl ether/acetonitrile/0.5% triethylamine (2:2:3:2, v/v/v/v) was selected for high-speed counter-current chromatography separation. The separation was initiated by filling the column with a mixture of intermediate phase and lower phase as a stationary phase followed by elution with upper phase to separate the hydrophobic compounds. Then the mobile phase was switched to the intermediate phase to elute the moderately hydrophobic compounds, and finally the polar compounds still retained in the column were fractionated by eluting the column with the lower phase. In this research, 12 peaks were eluted out in one-step operation within 110 min, among them, eight compounds with acceptable purity were obtained and identified. The purities of β-sitosterol, protopine, allocryptopine, isocorydione, isocorydine, coptisine, berberrubine, and berberine were 94.7, 96.5, 97.9, 86.6, 98.9, 97.6, 95.7, and 92.8%, respectively.

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Preparative enantioseparation of propafenone by counter-current chromatography using di-n -butyl l-tartrate combined with boric acid as the chiral selector

Cited by 8 publications

References 20 publications

Enantioseparations of three amino alcohols using a di-n-butyl-l-tartrate–boric acid complex as the mobile phase additive by reversed-phase high performance liquid chromatography

Enantioseparations of three amino alcohols using a di-n-butyl-l-tartrate–boric acid complex as the mobile phase additive by reversed-phase high performance liquid chromatography

Synergetic mechanism and enantioseparation of aromatic β‐amino acids by biphasic chiral high‐speed counter‐current chromatography

Three-phase solvent systems for the comprehensive separation of a wide variety of compounds fromDicranostigma leptopodumby high-speed counter-current chromatography

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