Some recent high-performance liquid chromatography separations of the enantiomers of pharmaceuticals and other compounds using the Whelk-O 1 chiral stationary phase

Welch, Christopher J.; Szczerba, Ted; Perrin, Scott R.

doi:10.1016/s0021-9673(96)00569-9

Cited by 78 publications

(40 citation statements)

References 21 publications

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“…Thereby, special phases for the chiral separation of bblockers [48] or NSAIDs [49][50][51], for example, were developed. The Whelk-O 1 CSP, prepared in the Pirkle lab and commercialized by Regis Technologies (Morton Grove, IL, USA), was shown to be applicable to a broad range of compounds [52].…”

Section: Direct Methodsmentioning

confidence: 99%

Chiral separation by chromatographic and electromigration techniques. A Review

Gübitz

Schmid

2001

Biopharm & Drug Disp

227

135

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This review gives a survey of different chiral separation principles and their use in high-performance liquid chromatography (HPLC), gas chromatography (GC), supercritical fluid chromatography (SFC), thin-layer chromatography (TLC), capillary electrophoresis (CE) and capillary electrochromatography (CEC) highlighting new developments and innovative techniques. The mechanisms of the different separation principles are briefly discussed and some selected applications are shown.

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Section: Direct Methodsmentioning

confidence: 99%

Chiral separation by chromatographic and electromigration techniques. A Review

Gübitz

Schmid

2001

Biopharm & Drug Disp

227

135

View full text Add to dashboard Cite

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“…HPLC methods have also been reported for the enantioselective analysis of IRD employing stationary phase based on a 1 -acid glycoprotein [7,8], tetra-hydrophenanthrene p-systems [9], cellulose 4-tert-butylphenylcarbamate [10] and polysaccharide derivatives [11]. In addition, an LC/MS method was reported for the determination of degradation products from IRD [12].…”

Section: Introductionmentioning

confidence: 99%

Capillary electrophoresis method for the determination of isradipine enantiomers: Stability studies and pharmaceutical formulation analysis

2011

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A simple enantioselective method based on CE using CD as chiral selector was developed and validated for the determination of isradipine (IRD) enantiomers in a pharmaceutical formulation and for the determination of IRD enantiomers in degradation studies. After optimization, the best results were obtained using 15 mM borate buffer at pH 9.3 and sulfobutyl ether-β-cyclodextrin (2.5%, w/v) as chiral selector. The applied voltage was +30 kV, and the sample injection was performed in the hydrodynamic mode. All analyses were carried out in a fused-silica uncoated capillary with an id of 50 μm and total length of 60.0 cm. Under these conditions, a complete separation between IRD enantiomers was achieved in less than 7 min. Linearity was obtained in the range 50-300 μg/mL for both enantiomers (r≥0.9978). The RSD (%) and relative errors (%) obtained in precision and accuracy studies (intra-day and inter-day) were lower than 5%. Therefore, this method was found to be appropriate for controlling pharmaceutical formulations containing IRD enantiomers and the assay was considered to be stability indicating. The drug was subjected to oxidation, hydrolysis and photolysis. In all stress conditions the drug presented considerable degradation when compared with a fresh sample (zero time).

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“…It was initially designed to separate naproxen; however, it has been shown to be useful for the separation of underivatized enantiomers of various classes of compounds such as amides, epoxides, esters, ureas, carbamates, ethers aziridines, phosphonates, aldehydes, ketones, carboxylic acids, alcohols, and nonsteroidal anti-inflammatory drugs (NSAIDs). [22][23][24] Separations on this CSP may be expected to utilize a combination of p-acidity, p-basicity, hydrogen bond donor/acceptor sites, and steric interactions for chiral recognition purposes. This stationary phase presents two stereogenic centers and the accepted mechanistic significance of this CSP suggests that the bulky substituents on vicinal stereogenic centers confer considerable rigidity to apparently hold the interaction sites in spatial positions that might enhance the chiral recognition properties.…”

Section: Introductionmentioning

confidence: 99%

High‐performance liquid chromatography separation of enantiomers of mandelic acid and its analogs on a chiral stationary phase

Aneja

Luthra

Ahuja³

2009

Chirality

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The enantiomers of mandelic acid and its analogs have been chromatographically separated on a chiral stationary phase (CSP) derived from 4-(3,5-dinitrobenzamido) tetrahydrophenanthrene. The rationale of separations of these compounds is discussed with respect to the method development for determining enantiomeric purity and possibility of obtaining enantiomerically pure materials by high-pressure liquid chromatography. The relationship of analyte structure to the extent of enantiomeric separation has been examined and separation factors (alpha) are presented for various groups of structurally related compounds. Chiral recognition models have been suggested to account for the observed separations. These models provide mechanistic insights into the chiral recognition process.

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Some recent high-performance liquid chromatography separations of the enantiomers of pharmaceuticals and other compounds using the Whelk-O 1 chiral stationary phase

Cited by 78 publications

References 21 publications

Chiral separation by chromatographic and electromigration techniques. A Review

Chiral separation by chromatographic and electromigration techniques. A Review

Capillary electrophoresis method for the determination of isradipine enantiomers: Stability studies and pharmaceutical formulation analysis

High‐performance liquid chromatography separation of enantiomers of mandelic acid and its analogs on a chiral stationary phase

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