Pharmaceutical-enantiomers resolution using immobilized polysaccharide-based chiral stationary phases in supercritical fluid chromatography

Klerck, Katrijn De; Heyden, Yvan Vander; Mangelings, Debby

doi:10.1016/j.chroma.2013.12.044

Cited by 42 publications

(21 citation statements)

References 25 publications

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“…The initial and new screening results confirm an observation made earlier in supercritical fluid chromatography . It was observed there that the complementarity and enantioselectivity of polysaccharide selectors, regardless being chlorinated or not, coated or immobilized, always results in a high cumulative success rate when applying three or four of them.…”

Section: Resultssupporting

confidence: 84%

A chiral separation strategy for acidic drugs in capillary electrochromatography using both chlorinated and nonchlorinated polysaccharide‐based selectors

et al. 2014

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A generic chiral separation strategy for the analysis of acidic compounds in CEC is proposed in completion of an earlier defined strategy for nonacidic compounds. The screening step of this strategy uses a 45 mM ammonium formate (pH 2.9)/ACN (35/65, v/v) mobile phase, a temperature of 25°C, and an applied voltage of 15 kV. To update the screening step, eight chiral stationary phases, which all possessed chlorinated and nonchlorinated polysaccharide-based chiral selectors, were evaluated using the earlier defined screening conditions. A combination of the two types of polysaccharide-based chiral phases proved to have the highest cumulative success rate. In the updated screening step, amylose tris(3,5-dimethylphenylcarbamate) (ADH), cellulose tris(4-methylbenzoate) (OJH), cellulose tris(3,5-dichlorophenylcarbamate) (SP5), and cellulose tris(3,5-dimethylphenylcarbamate) (ODRH) were included as selectors and their preferred screening sequence was determined as ADH > OJH > SP5 > ODRH. New optimization steps were also defined for SP5 by investigating the influences of different parameters on the separation outcome using an experimental design approach. After application of the updated strategy, 15 of 17 acidic pharmaceuticals were separated under screening conditions, of which 9 were baseline resolved. When the optimization steps were applied, another three compounds were baseline separated, while the total number of separations was increased by one, which brings the total number of separations to 16 of 17 with 12 baseline separated compounds. This reflects the successful performance of the updated strategy on acidic compounds.

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Section: Resultssupporting

confidence: 84%

A chiral separation strategy for acidic drugs in capillary electrochromatography using both chlorinated and nonchlorinated polysaccharide‐based selectors

et al. 2014

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“…Thus, in the last years a large number of separation (screening and optimizations steps) and chemiometric strategies for the enantioseparation of pharmaceuticals on polysaccharide-based CSPs in NP, 48 PO, 49,50 RP, 51 multimodal elution mode, 52 and SFC 53,54 has been reported. Four chromatographic method development platforms were used, among which were chiral SFC on 12 polysaccharide-based columns (150 × 4.6 mm, 3 μm) (mobile phases: 25 mM isobutylamine in ROH/CO 2 ).…”

Section: Halogens In Hplc Enantioseparationsmentioning

confidence: 99%

Liquid Chromatography Enantioseparations of Halogenated Compounds on Polysaccharide‐Based Chiral Stationary Phases: Role of Halogen Substituents in Molecular Recognition

2015

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Halogenated chiral molecules have become important in several fields of science, industry, and society as drugs, natural compounds, agrochemicals, environmental pollutants, synthetic products, and chiral supports. Meanwhile, the perception of the halogen moiety in organic compounds and its role in recognition processes changed. Indeed, the recognition of the halogen bond as an intermolecular interaction occurring when the halogen acts as a Lewis acid had a strong impact, particularly in crystal engineering and medicinal chemistry. Due to this renewed interest in the potentialities of chiral organohalogens, here we focus on selected recent applications dealing with enantioseparations of halogenated compounds on polysaccharide-based chiral stationary phases (CSPs), widely used in liquid chromatography (LC). In particular, recently the first case of halogen bonding-driven high-performance LC (HPLC) enantioseparation was reported on a cellulose-based CSP. Along with enantioseparations performed under conventional HPLC, representative applications using supercritical fluid chromatography (SFC) are reported.

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“…Among these developed CSPs, polysaccharide‐derived CSPs, especially cellulose analogues as chiral selectors, exhibit a wide range of applications . Furthermore, compared with coated polysaccharide‐derived CSPs, immobilized‐type CSPs make the application range wider due to their wide range of mobile phase selection and good stability . As the immobilized polysaccharide‐derived CSPs, Chiralpak IC column is prepared by bonding a cellulose tris‐(3,5‐dichlorophenylcarbamate) derivative to a silica gel matrix.…”

Section: Introductionmentioning

confidence: 99%

Separation of eight bedaquiline analogue diastereomers by HPLC on an immobilized polysaccharide‐based chiral stationary phase

Jiang

et al. 2018

Chirality

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The high‐performance liquid chromatography (HPLC) is a powerful method in the area of stereoisomer separation. In this study, separation of eight bedaquiline analogue diastereomers (compounds 1‐8) was first examined on a cellulose tris‐(3,5‐dichlorophenylcarbamate) chiral stationary phase, ie, Chiralpak IC in the normal phase mode. The influences of organic modifier types, alcohol content, and column temperature on diastereoseparation were evaluated. Under the optimum chromatographic conditions, all the analyte stereoisomers were successfully separated. The experimental results revealed the great influence of analytes' structures on the diastereoseparation with Chiralpak IC. In addition, thermodynamic parameters were calculated by Van't Hoff plots, and correlative chiral recognition mechanisms were discussed further.

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Pharmaceutical-enantiomers resolution using immobilized polysaccharide-based chiral stationary phases in supercritical fluid chromatography

Cited by 42 publications

References 25 publications

A chiral separation strategy for acidic drugs in capillary electrochromatography using both chlorinated and nonchlorinated polysaccharide‐based selectors

A chiral separation strategy for acidic drugs in capillary electrochromatography using both chlorinated and nonchlorinated polysaccharide‐based selectors

Liquid Chromatography Enantioseparations of Halogenated Compounds on Polysaccharide‐Based Chiral Stationary Phases: Role of Halogen Substituents in Molecular Recognition

Separation of eight bedaquiline analogue diastereomers by HPLC on an immobilized polysaccharide‐based chiral stationary phase

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