Advances in enantioselective separations using electromigration capillary techniques

Preinerstorfer, Beatrix; Lämmerhofer, Michael; Lindner, Wolfgang

doi:10.1002/elps.200800607

Cited by 148 publications

(114 citation statements)

References 142 publications

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“…[24][25][26] In CE separation, typically chiral selectors, such as CDs, proteins and chiral surfactants, are added to the running buffers. [26][27][28][29] Among various chiral selectors, successful enantiomer separations of some NSAIDs have been reported by employing dextrin as a chiral selector. 19,20 The CE enantiomer separation of NSAIDs was investigated by employing dextrin.…”

Section: Enantiomer Separation Of Nsaids By Ce With Dextrinmentioning

confidence: 99%

High-performance Enantiomer Separation of Nonsteroidal Anti-inflammatory Drugs (NSAIDs) by 3 μm Reversed-phase Chiral Columns and Application to the Optical Purity Testing of Naproxen Drug Substances and Its Formulations

2014

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The enantiomer separation of five nonsteroidal anti-inflammatory drugs (NSAIDs), such as ibuprofen, ketoprofen (KP) and naproxen (NX), which are included in The Japanese Pharmacopoeia 16th edition (JP16), was investigated by employing four kinds of 3 μm reversed-phase chiral columns (AD-3R, AS-3R, OD-3R and OJ-3R). Except for KP, the enantiomers of four NSAIDs were successfully separated by one of the four columns. Among five NSAIDs, only NX has been used as a single enantiomer (S-form, active form) in the clinical field (JP16); therefore, optical purity testing method of NX is required for its quality evaluation. Among four CSPs, the method was developed by using an AS-3R column, which showed good enantioselectivity for NX enantiomers. By optimizing the conditions, the resolution (Rs) of 2.55 was obtained for NX enantiomers within approximately 6 min. The minor enantiomer R-form eluted before the main active enantiomer S-form. Finally, the developed method was applied to the optical purity testing of NX active pharmaceutical ingredients (APIs), and its formulations (tablet and capsule). Other than the minor enantiomer (R-form, inactive form, 0.21 -0.78%), normal (not chiral) impurities at levels of 0.01 -0.3% were simultaneously separated and determined by the method, showing an excellent separation capability of the method for those impurities including the minor enantiomer. The content uniformity test of the NX tablet according to JP16 was also successfully performed by the method with the AS-3R column. Normal phase separation with two chiral columns (AD-H and OD-H) and capillary electrophoretic (CE) separation were also investigated for five NSAIDs enantiomers to discuss the enantioselectivity.

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Section: Enantiomer Separation Of Nsaids By Ce With Dextrinmentioning

confidence: 99%

High-performance Enantiomer Separation of Nonsteroidal Anti-inflammatory Drugs (NSAIDs) by 3 μm Reversed-phase Chiral Columns and Application to the Optical Purity Testing of Naproxen Drug Substances and Its Formulations

2014

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“…[5][6][7] In the direct separation mode different types of chiral selectors, such as cyclodextrines, macrocyclic antibiotics, carbohydrates, chiral crown ethers, calixarenes, proteins and chiral metal complexes (Ligand-exchange) are most commonly used as chiral selectors. [8][9][10][11][12] The principle of ligand-exchange is based on the formation of diastereomeric ternary mixed metal com- plexes between the chiral selector ligand and the analyte and was first introduced by Davankov and Roghozin in the late 1960s-early 1970s for conventional columns. 13 Zare and co-workers transformed this principle to CE using histidine or aspartame-Cu(II) complexes for the resolution of racemic mixtures of Dns-AAs in the late 1980s.…”

Section: Introductionmentioning

confidence: 99%

Enantioseparation of Dansylated Amino Acids by Ligand-exchange Capillary Electrophoresis Using L-phenylalaninamide, L-lysine or L-threonine as Chiral Selector

Mohr¹,

Hägele²,

Schmid³

2011

Croat. Chem. Acta

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Abstract. In recent years enantioseparation of both active pharmaceutical ingredients and bio molecules such as amino acids became more and more necessary because in most cases the two stereo forms exhibit different pharmacological effects. This article deals with the chiral separation of dansylated amino acids by ligand-exchange capillary electrophoresis using L-phenylalaninamide, L-lysine and L-threonine as chiral selectors. Experiments with different central metal ions such as Cu(II), Co(II), Cd(II), Ni(II) and Zn(II) were carried out. Optimal conditions were found out by studying the effect of the pH and the selector molarity on the chiral resolution. Best separation was obtained for the Cu(II)/L-lysine complex, showing a chiral resolution up to 17 for Dns-DL-Met. (doi: 10.5562/cca1762)

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“…See for example, the recent review by Lindner and coworkers. 2 This shortcoming can, however, be overcome by using conductivity detection, which is universal for all ionic species.…”

Section: Introductionmentioning

confidence: 99%

Following the lipase catalyzed enantioselective hydrolysis of amino acid esters with capillary electrophoresis using contactless conductivity detection

Schuchert‐Shi

Hauser

2009

Chirality

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The progress of the enzymatic hydrolysis of racemic mixtures of the enantiomers of the methyl esters of serine and threonine was monitored. This was possible in a reaction vessel of 1.5 mL by direct sampling of volumes in the nanoliter-range directly into an electrophoresis capillary. Contactless conductivity detection was used for quantification as the analytes are not accessible by UV-detection in capillary electrophoresis. Porcine pancreatic lipase and wheat germ lipase both showed a preference for the L-enantiomers of both amino acid esters. The selectivity of the porcine lipase between the two L-esters of the two amino acids was also studied and it was found that the production of L-threonine had priority over L-serine. Chirality 22:331-335, 2010. V V C 2009 Wiley-Liss, Inc.

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Advances in enantioselective separations using electromigration capillary techniques

Cited by 148 publications

References 142 publications

High-performance Enantiomer Separation of Nonsteroidal Anti-inflammatory Drugs (NSAIDs) by 3 μm Reversed-phase Chiral Columns and Application to the Optical Purity Testing of Naproxen Drug Substances and Its Formulations

High-performance Enantiomer Separation of Nonsteroidal Anti-inflammatory Drugs (NSAIDs) by 3 μm Reversed-phase Chiral Columns and Application to the Optical Purity Testing of Naproxen Drug Substances and Its Formulations

Enantioseparation of Dansylated Amino Acids by Ligand-exchange Capillary Electrophoresis Using L-phenylalaninamide, L-lysine or L-threonine as Chiral Selector

Following the lipase catalyzed enantioselective hydrolysis of amino acid esters with capillary electrophoresis using contactless conductivity detection

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