The degree of substitution affects the enantioselectivity of sulfobutylether‐β‐cyclodextrin chiral stationary phases

Folprechtová, Denisa; Kalíková, Květa; Kozlík, Petr; Tesařová, Eva

doi:10.1002/elps.201800471

Cited by 19 publications

(7 citation statements)

References 34 publications

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“…Folprechtová et al [ 43 ] prepared by dynamic coating three new CSPs based on sulfobutylether-β-cyclodextrin derivatives ( Figure 2 C), with different degrees of substitution. The new CSPs presented a great enantioselectivity.…”

Section: Coating Methodsmentioning

confidence: 99%

Strategies for Preparation of Chiral Stationary Phases: Progress on Coating and Immobilization Methods

et al. 2021

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Enantioselective chromatography is one of the most used techniques for the separation and purification of enantiomers. The most important issue for a specific successful enantioseparation is the selection of the suitable chiral stationary phase (CSP). Different synthetic approaches have been applied for the preparation of CSPs, which embrace coating and immobilization methods. In addition to the classical and broadly applied coating and immobilization procedures, innovating strategies have been introduced recently. In this review, an overview of different methods for the preparation of coated and immobilized CSPs is described. Updated examples of CSPs associated with the various strategies are presented. Considering that after the preparation of a CSP its characterization is fundamental, the methods used for the characterization of all the described CSPs are emphasized.

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Section: Coating Methodsmentioning

confidence: 99%

Strategies for Preparation of Chiral Stationary Phases: Progress on Coating and Immobilization Methods

et al. 2021

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“…Coating sulfobutylether-cyclodextrin with different degrees of substitutions (4, 6.3, and 10) onto strong anion exchange stationary phases (silica-based quaternary ammonium-bound sorbent), for the preparation of CSPs, was an approach reported by Folprechtová et al [ 92 ]. The ES potential and stability of the developed CSP was evaluated with the chiral drugs oxazepam, lorazepam, promethazine, thioridazine, carprofen, fenoprofen, flurbiprofen, indoprofen, as well as 6-hydroxyflavanone, 7-hydroxyflavanone, tert -butyloxycarbonyl-tryptophan, Tröger’s base, propranolol, and 5-fluor-tryptophan, employing reversed phase/polar organic mode HPLC (methanol/formic acid, pH 2.10, and methanol/10 mM ammonium acetate buffer, pH 4.00, in various volume ratios).…”

Section: β-Cyclodextrin-based Cspsmentioning

confidence: 99%

Polysaccharide- and β-Cyclodextrin-Based Chiral Selectors for Enantiomer Resolution: Recent Developments and Applications

Bui

Rosenau

2021

Molecules

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Polysaccharides, oligosaccharides, and their derivatives, particularly of amylose, cellulose, chitosan, and β-cyclodextrin, are well-known chiral selectors (CSs) of chiral stationary phases (CSPs) in chromatography, because they can separate a wide range of enantiomers. Typically, such CSPs are prepared by physically coating, or chemically immobilizing the polysaccharide and β-cyclodextrin derivatives onto inert silica gel carriers as chromatographic support. Over the past few years, new chiral selectors have been introduced, and progressive methods to prepare CSPs have been exploited. Also, chiral recognition mechanisms, which play a crucial role in the investigation of chiral separations, have been better elucidated. Further insights into the broad functional performance of commercially available chiral column materials and/or the respective newly developed chiral phase materials on enantiomeric separation (ES) have been gained. This review summarizes the recent developments in CSs, CSP preparation, chiral recognition mechanisms, and enantiomeric separation methods, based on polysaccharides and β-cyclodextrins as CSs, with a focus on the years 2019–2020 of this rapidly developing field.

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“…Limited number of literatures reported other substituted β‐cyclodextrins such as hydroxyethyl‐β‐cyclodextrin [21], carboxymethyl‐β‐cyclodextrin [24,34,35], sulfated‐β‐cyclodextrin [36,37], and methyl‐β‐cyclodextrin [38]. Sulfobutyl ether‐β‐cyclodextrin showed impressive high enantiorecognition in the separation of N‐alkyl alkaline compounds as an anionic β‐cyclodextrin in traditional chiral liquid chromatography [39–42] and chiral capillary electrophoresis [43–46]. However, only three papers have been published so far with regard to enantioseparation by countercurrent chromatography using sulfobutyl ether‐β‐cyclodextrin as chiral selector [19,47,48], and only one literature reporting its use in enantioseparation of alkaline racemate by countercurrent chromatography [47].…”

Section: Introductionmentioning

confidence: 99%

Enantioseparation of ondansetron by countercurrent chromatography using sulfobutyl ether‐β‐cyclodextrin as chiral selector

Sun

Bao

Qian

et al. 2021

J of Separation Science

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Ondansetron, a highly selective 5‐hydroxytryptamine 3 receptor antagonist, was successfully enantioseparated by recycling countercurrent chromatography using sulfobutyl ether‐β‐cyclodextrin as chiral selector. Important factors for the enantioseparation were optimized, including different organic solvent, type of substituted β‐cyclodextrin, pH of aqueous phase, concentration of chiral selector, and separation temperature. A biphasic solvent system composed of n‐hexane: n‐butyl acetate: 0.1 mol/L phosphate buffer solution pH 9.2 with 50 mmol/L of sulfobutyl ether‐β‐cyclodextrin (2.5:7.5:10, v/v/v) was selected. Under optimized separation conditions, 5 mg of ondansetron was enantioseparated using recycling countercurrent chromatography, yielding 1.2 and 1.5 mg of ondansetron enantiomers with 97.5 and 95.8% purity and the recovery reached 48–60%.

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The degree of substitution affects the enantioselectivity of sulfobutylether‐β‐cyclodextrin chiral stationary phases

Cited by 19 publications

References 34 publications

Strategies for Preparation of Chiral Stationary Phases: Progress on Coating and Immobilization Methods

Strategies for Preparation of Chiral Stationary Phases: Progress on Coating and Immobilization Methods

Polysaccharide- and β-Cyclodextrin-Based Chiral Selectors for Enantiomer Resolution: Recent Developments and Applications

Enantioseparation of ondansetron by countercurrent chromatography using sulfobutyl ether‐β‐cyclodextrin as chiral selector

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