Enantiomeric resolution of multiple chiral centres racemates by capillary electrophoresis

Ali, Imran; Suhail, Mohd; ALOthman, Zeid A.; Al–Warthan, Abdulrahman; Aboul‐Enein, Hassan Y.

doi:10.1002/bmc.3691

Cited by 50 publications

(18 citation statements)

References 94 publications

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“…Different kinds of chiral stationary phase (CSP) have been developed and reported to achieve enantiomeric separation of various chiral drugs . Polysaccharide‐based CSPs are significant because of their broad application and brilliant loading capacity . Among them, cellulose tris‐(3,5‐dichlorophenylcarbamate) (CDCPC) has been known as a CSP with high enantiorecognition ability since the 1980s .…”

Section: Introductionmentioning

confidence: 99%

Enantioseparation and molecular modeling study of five β‐adrenergic blockers on Chiralpak IC column

Zhao

Wang

et al. 2019

Chirality

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A new high‐performance liquid chromatography (HPLC) method was developed for the enantiomeric resolution of five β‐adrenergic blockers on a Chiralpak IC column (250 mm × 4.6 mm, 5.0 μm particle size) in normal phase mode. The mobile phase used was n‐hexane‐ethanol‐diethylamine in different proportions at the flow rate of 1.0 mL/min with the column temperature of 25°C using a UV detector at 230 nm. The influences of base additives and alcohol modifiers were evaluated and optimized. The maximum resolution values for bevantolol, propranolol carteolol, esmolol, and metoprolol were 4.80, 2.77, 2.09, 2.30, and 1.11, respectively. To gain a better understanding of the interaction between chiral stationary phase and analyte enantiomers, the molecular docking of chiral stationary phase with five pairs of enantiomer was carried out using AutoDock molecular docking technique. By simulation studies, the mechanism of chiral recognition was determined. According to the results, hydrogen bond interactions and π‐π interactions were the chief interactions for the chiral recognition.

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Section: Introductionmentioning

confidence: 99%

Enantioseparation and molecular modeling study of five β‐adrenergic blockers on Chiralpak IC column

Zhao

Wang

et al. 2019

Chirality

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“…[11][12][13][14][15][16] Many papers have been published on the racemates with 1 chiral center. 24,25 It is due to the fact that the enantiomeric resolution is extremely tricky of the racemates with greater than 1 chiral center, owing to identical properties of the enantiomers. 24,25 It is due to the fact that the enantiomeric resolution is extremely tricky of the racemates with greater than 1 chiral center, owing to identical properties of the enantiomers.…”

Section: Introductionmentioning

confidence: 99%

Enantiomeric resolution and modeling of DL‐alanine‐DL‐tryptophan dipeptide on amylose stationary phase

et al. 2018

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The enantiomeric resolution of DL-alanine-DL-tryptophan dipeptide is described on amylose stationary phase. The eluent used was CH OH─CH COONH (10mM)─CH CN (50: 40, 10) at 0.8-mL/min flow, 230-nm detection, 25-minute run time, and 25°C ± 1°C temperature. The chiral phase was amylose [AmyCoat RP (15 cm × 0.46 cm × 5 micron)]. The magnitudes of the retention factors (k) were 2.71, 3.52, 5.11, and 7.75. The magnitudes of separation factor (α) were 1.19, 1.57, and 1.51 while the resolution factors (Rs) were 3.25, 14.84, and 15.76. The limits of detection and quantitation were of 2.5 to 5.4 and 12.8 to 27.5 μg/mL. The enantiomeric resolution is controlled by hydrogen, hydrophobic, π-π, steric, etc interactions. The elution order of the enantiomer was supported by the modeling data. The described method is fast, reproducible, precise, and selective, which can be used successfully for evaluating the enantiomers of the reported dipeptide.

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“…Development of enantioseparation techniques has great significance from the point of view of performance in biological environments and in several industries including pharmaceutical, agricultural and food chemistry . So far, numerous analytical techniques have been developed for chiral separation, including, GC , SFC , HPLC and CE . High efficiency, fast analysis, and the minimum consumption of buffer and samples are the most important advantages of CE which makes it an appropriate candidate for the enantioseparation.…”

Section: Introductionmentioning

confidence: 99%

Evaluation of the synergistic effect with amino acids for enantioseparation of basic drugs using capillary electrophoresis

et al. 2018

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The synergistic effect of two acidic amino acids, aspartic and glutamic acid, on the electrophoretic enantioseparation of four basic drugs was evaluated in the BGE containing a CD and at different pHs. Chlorpheniramine, hydroxyzine, propranolol and tramadol were used as the basic model drugs. However, no enantioseparations were achieved with a BGE containing sole amino acid, but the combined use of an acidic amino acid and a CD showed improved enantioseparations (synergistic effect) compared with the single CD system. The results demonstrated that at optimized pH, the electrostatic interactions of the anionic amino acids with the positively charged basic drugs could result in a decrease of the analyte migration velocity and it consequently improved the enantioseparation. The effective parameters such as the amino acid and chiral selector type and concentration, buffer pH, applied voltage, and capillary temperature were optimized. Favorable enantiomeric resolution and migration times of the model drugs were achieved with a 100 mM phosphate buffer solution (pH 3.0) containing 5.0 mM HP-α-CD/HP-β-CD and 20 mM aspartic acid with an 18 kV applied voltage at 25°C. H NMR experiments were also carried out in a mixture of an analyte and CD in the absence and presence of aspartic acid. The NMR results were consistent with the results obtained by CE which showed the synergistic effect of amino acid.

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Enantiomeric resolution of multiple chiral centres racemates by capillary electrophoresis

Cited by 50 publications

References 94 publications

Enantioseparation and molecular modeling study of five β‐adrenergic blockers on Chiralpak IC column

Enantioseparation and molecular modeling study of five β‐adrenergic blockers on Chiralpak IC column

Enantiomeric resolution and modeling of DL‐alanine‐DL‐tryptophan dipeptide on amylose stationary phase

Evaluation of the synergistic effect with amino acids for enantioseparation of basic drugs using capillary electrophoresis

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