Chapter 9 Recent developments in liquid chromatographic enantioseparation

Lämmerhofer, Michael; Lindner, Wolfgang

doi:10.1016/s1567-7192(00)80012-1

Cited by 23 publications

(19 citation statements)

References 488 publications

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“…Such stationary phases based upon the immobilization of macrocyclic antibiotics and proteins in their natural or modified forms [1][2][3][4][5] are, however, known to suffer from a low number of specific binding sites, poor efficiencies and limited stabilities [2]. To overcome these problems, a promising approach consists in using low molecular weight chiral ion exchangers as chromatographic ligands for enantioseparations [6]. Cysteine, an amino acid with thiol group that can be easily oxidized to form a chiral strong cation exchanger (SCX), could be used toward this aim.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective strong cation‐exchange molecular recognition materials: Design of novel chiral stationary phases and their application for enantioseparation of chiral bases by nonaqueous capillary electrochromatography

et al. 2003

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New chiral stationary phases derived from enantiomerically pure derivatives of cysteine carrying sulfonic acid groups are synthesized and evaluated for enantiomer separation of chiral bases by non aqueous capillary electrochromatography after bonding to a linker and grafting upon thiol-modified silica particles. Structural modifications of these low molecular weight chiral selectors are investigated and discussed in terms of apparent enantioselectivities and resolution factors based on the enantiomeric separations of a set of chiral bases including beta-blockers, beta-sympathomimetics and other basic drugs. The influence of the mobile phase constitution and its flow velocity on the enantioseparation by nonaqueous capillary electrochromatography is also briefly evaluated and discussed for the chiral substances investigated.

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Section: Introductionmentioning

confidence: 99%

Enantioselective strong cation‐exchange molecular recognition materials: Design of novel chiral stationary phases and their application for enantioseparation of chiral bases by nonaqueous capillary electrochromatography

et al. 2003

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“…Numerous strategies are available for enantioseparations [3][4][5][6] that are well documented in the literature and applied in combination with various separation techniques, such as (i) liquid, gas, thin layer, or supercritical fluid chromatography and (ii) electrophoretic methods (i.e., capillary electrophoresis or electrochromatography). 7,8 The possibility of speeding up the enantioseparation process is an attractive goal in the pharmaceutical field. For example, there is a need to develop fast analytical methods for real-time monitoring of raw materials and final products.…”

Section: 2mentioning

confidence: 99%

Fast chiral separation of drugs using columns packed with sub‐2 μm particles and ultra‐high pressure

et al. 2009

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The use of columns packed with sub-2 lm particles in liquid chromatography with very high pressure conditions (known as UHPLC) was investigated for the fast enantioseparation of drugs. Two different procedures were evaluated and compared using amphetamine derivatives and b-blockers as model compounds. In one case, cyclodextrins (CD) were directly added to the mobile phase and chiral separations were carried out in less than 5 min. However, this strategy suffered from several drawbacks linked to column lifetime and low chromatographic efficiencies. In the other case, the analysis of enantiomers was carried out after a derivatization procedure using two different reagents, 2,3,4-tri-O-acetyl-a-D-arabinopyranosyl isothiocyanate (AITC) and N-a-(2,4-dinitro-5-fluorophenyl)-L-alaninamide (Marfey's reagent). Separation of several amphetamine derivatives contained within the same sample was achieved in 2-5 min with high efficiency and selectivity. The proposed approach was also successfully applied to the enantiomeric purity determination of (1)

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“…As more versatile chiral stationary phases are available for HPLC, this technique is more prominent and user friendly to monitor the enantiomeric purity of chiral drug substance. Among available chiral stationary phases, most of chiral separations were reported by using derivatized polysaccharides [10]- [12].…”

Section: Introductionmentioning

confidence: 99%

A New and Enantioselective Chromatographic Method for Linagliptin on Amylose Coated Chiral Stationary Phase

Kumar¹,

Aparna²,

Vasa³

et al. 2016

AJAC

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A new and enantioselective liquid chromatographic method was developed for estimation of S-Linagliptin in Linagliptin (LINA) drug substances. The desired enantiomeric separation was achieved on Chiralpak AD-H (250 * 4.6 mm * 5 µm) column with the mobile phase composition of ethanol, methanol and diethylamine in a ratio of 90:10:0.1 (v/v/v) with flow rate of 0.5 mL•min −1 and column oven temperature 30˚C and the eluted compounds were monitored at 225 nm. In the proposed chiral method, USP resolutions between both the enantiomers were more than 5.0. Limit of detection and Limit of quantitation of S-LINA was found to be 0.03 µg•mL −1 and 0.10 µg•mL −1 respectively. Linearity study was conducted from LOQ to 150% and correlation coefficient found to be 0.9997. Accuracy was within the range of 98.6% to 101.5%. To prove selectivity power of the method specificity study was conducted by subjecting drug substance to acid, base, hydrolysis, oxidation and photolysis and ensured the peak purity of analyte in degraded samples. Moreover, the method has been fully validated as per ICH guidelines. The proposed method is precise, accurate, linear, rugged, robust and suitable for accurate quantification of S-LINA in LINA drug substance.

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Chapter 9 Recent developments in liquid chromatographic enantioseparation

Cited by 23 publications

References 488 publications

Enantioselective strong cation‐exchange molecular recognition materials: Design of novel chiral stationary phases and their application for enantioseparation of chiral bases by nonaqueous capillary electrochromatography

Enantioselective strong cation‐exchange molecular recognition materials: Design of novel chiral stationary phases and their application for enantioseparation of chiral bases by nonaqueous capillary electrochromatography

Fast chiral separation of drugs using columns packed with sub‐2 μm particles and ultra‐high pressure

A New and Enantioselective Chromatographic Method for Linagliptin on Amylose Coated Chiral Stationary Phase

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