High performance liquid chromatographic enantioseparation development and analytical method characterization of the carboxylate ester of evacetrapib using an immobilized chiral stationary phase with a non-conventional eluent system

Sharp, V. Scott; Gokey, Megan A.; Wolfe, Chad N.; Rener, Gregory A.; Cooper, Mary R.

doi:10.1016/j.chroma.2015.09.013

Cited by 9 publications

(4 citation statements)

References 31 publications

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“…As demonstrated in previous studies [16], nonstandard mobile-phase systems have many benefits. For instance, different selectivity profile may be achieved owing to the presence of solvents with diverse nature and properties.…”

Section: Resultsmentioning

confidence: 99%

“…Many separation technologies such as capillary electrophoresis (CE) [7,8], supercritical fluid chromatography (SFC) [9], capillary electrochromatography (CEC) [10], gas chromatography (GC) [11], and high-performance liquid chromatography (HPLC) [12,13,14,15] have been developed for obtaining efficient chiral separation for DHP enantiomers. Among all these separation techniques, HPLC remains predominant in the analytical scale enantioseparation arena [16]. Moreover, HPLC using chiral stationary phases (CSPs) is the most widely used technique for the direct analysis of enantiomers [17].…”

Section: Introductionmentioning

confidence: 99%

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Direct Enantiomeric Resolution of Seventeen Racemic 1,4-Dihydropyridine-Based Hexahydroquinoline Derivatives by HPLC

Sun

Gündüz

Zhang

et al. 2019

IJMS

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1,4-Dihydropyridine (DHP) scaffold holds an outstanding position with its versatile pharmacological properties among all heterocyclic compounds. Although most of the commercially available DHPs are marketed as a racemic mixture, the chiral center at C-4 can lead to even opposite pharmacological activities between the enantiomers. In the present study, enantioseparation of seventeen DHP structural analogues, consisting of either pharmacologically active or newly synthesized derivatives, (M2-4, MD5, HM2, HM10, CE5, N11, N10, N7, M11, MC6-8, MC13, MD23, and 42IIP) by high-performance liquid chromatography was investigated using immobilized polysaccharide-based chiral stationary phase, Chiralpak IC column. Due to the solvent versatility of the covalently immobilized chiral stationary phase in enantiomer separation, multiple elution modes including standard normal phase, nonstandard mobile phase, and reversed phase were used to expand the possibility to find the optimum enantioselective conditions for the tested analytes. Under appropriate separation conditions, complete enantiomeric separation was obtained for nearly all compounds except MC6-8 and MC13 which contained two chiral centers. Additionally, the effects of the polar modifier, the additive, and column temperature on the chiral recognition were evaluated. The thermodynamic parameters calculated according to the linear van’t Hoff equation indicated that the chiral separations in this study were enthalpy-driven or entropy-driven. Some parameters of method validation such as linearity, limit of quantitation, and repeatability were also measured for all studied compounds to prove the reliability of the method.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Direct Enantiomeric Resolution of Seventeen Racemic 1,4-Dihydropyridine-Based Hexahydroquinoline Derivatives by HPLC

Sun

Gündüz

Zhang

et al. 2019

IJMS

View full text Add to dashboard Cite

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“…have also been determined, especially in commercial products or biological samples (pharmaceutical formulations, human urine, human or animal blood, human plasma, animal serum, etc.). Another heterogeneous group of analytes, including connectors for building metal-organic frameworks [116,117,124], intermediates for the synthesis of pharmaceuticals [111], natural and synthetic compounds [39,113,121,120], biological compounds [82,112,58,71,78,86,[61][62][63]77,75], natural alkaloids [121], biomolecules [115,54], organometallic compounds [119] and chiral metabolites [103,108,100,97,102,59,63,52] has been enantioseparated with these immobilized polysaccharides CSPs (see Table 2-4). Fig.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

State-of-the-art and recent developments of immobilized polysaccharide-based chiral stationary phases for enantioseparations by high-performance liquid chromatography (2013–2017)

Padró

Keunchkarian

2018

Microchemical Journal

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Please cite this article as: Juan M. Padró, Sonia Keunchkarian , State-of-the-art and recent developments of immobilized polysaccharide-based chiral stationary phases for enantioseparations by high-performance liquid chromatography (2013)(2014)(2015)(2016)(2017). AbstractPolysaccharide-based chiral stationary phases have been recognized as one of the most powerful ones for high performance liquid chromatography (HPLC) separations of chiral compounds in analytical and also in preparative scale.Immobilized polysaccharide-based chiral stationary phases constitute a remarkable achievement due to their stable nature on working with standard or common solvents and also with those prohibited for using with coated phases.This review is mainly focused on the i. applications of these chiral stationary phases in numerous fields of HPLC separations; ii. comparative aspects between immobilized vs. coated polysaccharide-derived phases, and iii. revision of several theoretical studies such as enantiorecognition mechanism, mobile phase composition and column temperature effects.

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“…Enantioseparation is thus implemented by the chiral recognition between the chiral selector and chiral compound enantiomers. Among commercialized CSPs, those made from the derivatives of cellulose and amylose have attracted much more attention, due to their strong chiral recognition capability and wide applicability [6,7,8,9]. To date, lots of works on the preparation, chiral recognition mechanism and application of the CSPs derived from cellulose and amylose have been reported [10,11,12,13], and on those of the CSPs made with cellulose tris(3,5-dimethylphenylcarbamate) (CDMPC) and amylose tris(3,5-dimethylphenylcarbamate) (ADMPC) in particular [14,15,16,17].…”

Section: Introductionmentioning

confidence: 99%

Eluent Tolerance and Enantioseparation Recovery of Chiral Packing Materials Based on Chitosan Bis(Phenylcarbamate)-(n-Octyl Urea)s for High Performance Liquid Chromatography

et al. 2016

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Abstract:The goal of the present work was to study the influence of the swelling of chitosan derivatives on the enantioseparation and the separation performance recovery of chiral stationary phases (CSPs) based on these derivatives. Therefore, six chitosan bis(phenylcarbamate)-(n-octyl urea)s were synthesized, which were coated on macroporous 3-aminopropyl silica gel affording new CSPs. Most of the CSPs demonstrated strong enantioseparation capability for the tested chiral compounds. The swelling capacity of the chitosan bis(phenylcarbamate)-(n-octyl urea)s in ethyl acetate, acetone and tetrahydrofuran (THF) was evaluated. Among the chitosan derivatives, the chitosan bis(3,5-dichlorophenylcarbamate)-(n-octyl urea) polymer showed the highest swelling capacity in ethyl acetate and THF. The polymer-based CSPs could be utilized with pure ethyl acetate and a normal phase containing 70% THF, but was damaged by pure THF. On the other hand, the separation performance of the damaged CSP could be recovered after it was allowed to stand for a period of time. The observations are important for the development and application of polysaccharide derivative-based CSPs.

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High performance liquid chromatographic enantioseparation development and analytical method characterization of the carboxylate ester of evacetrapib using an immobilized chiral stationary phase with a non-conventional eluent system

Cited by 9 publications

References 31 publications

Direct Enantiomeric Resolution of Seventeen Racemic 1,4-Dihydropyridine-Based Hexahydroquinoline Derivatives by HPLC

Direct Enantiomeric Resolution of Seventeen Racemic 1,4-Dihydropyridine-Based Hexahydroquinoline Derivatives by HPLC

State-of-the-art and recent developments of immobilized polysaccharide-based chiral stationary phases for enantioseparations by high-performance liquid chromatography (2013–2017)

Eluent Tolerance and Enantioseparation Recovery of Chiral Packing Materials Based on Chitosan Bis(Phenylcarbamate)-(n-Octyl Urea)s for High Performance Liquid Chromatography

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