Isopropyl derivative of cyclofructan 6 as chiral selector in liquid chromatography and capillary electrophoresis

Maier, Vítězslav; Kalíková, Květa; Přibylka, Adam; Vozka, Jiří; Smuts, Jonathan; Švidrnoch, Martin; Ševčı́k, Juraj; Armstrong, Daniel W.; Tesařová, Eva

doi:10.1016/j.chroma.2014.02.061

Cited by 23 publications

(19 citation statements)

References 14 publications

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“…The composition of alkaline BGE (100 mM sodium borate pH 10.0) and the use of IP‐CF6 as a chiral selector for the separation of R,S‐ BNP were taken from Maier et al. . In our first experiments, using the set‐up shown in Fig.…”

Section: Resultsmentioning

confidence: 99%

Fast separation of enantiomers by capillary electrophoresis using a combination of two capillaries with different internal diameters

Šebestová

Petr

2017

Electrophoresis

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The combination of capillaries with different internal diameters was used to accelerate the separation of enantiomers in capillary electrophoresis. Separation of R,S-1,1'-binaphthalene-2,2'-diyl hydrogen phosphate using isopropyl derivative of cyclofructan 6 was studied as a model system. The best separation conditions included 500 mM sodium borate pH 9.5 with 60 mM concentration of the chiral selector. Separation lasted approx. 1.5 min using the combination of 50 and 100 μm id capillaries of 9.7 cm and 22.9 cm, respectively. It allowed approx. 12-fold acceleration in comparison to the traditional long-end separation mainly due to the higher electroosmotic flow generated in the connected capillaries.

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Section: Resultsmentioning

confidence: 99%

Fast separation of enantiomers by capillary electrophoresis using a combination of two capillaries with different internal diameters

Šebestová

Petr

2017

Electrophoresis

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“…All studied CSs (CF6, CF7, IP‐CF6, IP‐CF7, α‐CD and β‐CD) were uncharged at this pH and migrated at the EOF mobility, that is in the opposite direction to the R , S ‐BNP migration. In the previously published work , the composition of BGEs for the separation of BNP atropisomers using IP‐CF6 was studied and 50 mM sodium phosphate pH 2.5 was reported as the best acidic BGE. Therefore, this BGE was used for the current study of the comparison of CSs enantioselectivity in the acidic environment.…”

Section: Resultsmentioning

confidence: 99%

“…The electroosmotic mobility was higher than that of the R , S ‐BNP electrophoretic mobility, therefore a positive polarity voltage was applied. The composition of alkaline BGE, 100 mM sodium borate pH 10.0, was taken from previously published work . The amount of each CS required to obtain the baseline separation (in case of native CF7 the separation with the best achievable resolution) of R , S ‐BNP was higher than for the enantioseparation performed in the acidic BGE.…”

Section: Resultsmentioning

confidence: 99%

“…On the other side, low stability of sulfated CFs in the BGE due to the hydrolysis of the sulfate groups is a significant drawback. Recently, we published the work scoped on the comparison of the enantioselectivity of CF6 derivative isopropyl carbamate CF6 (IP‐CF6) in HPLC (as CSP) and CE (as BGE additive) for non‐polar atropisomers of selected binaphthyl derivatives . IP‐CF6 exhibited excellent enantioselectivity when immobilized as CSP in comparison to CE where IP‐CF6 was freely mobile in BGE.…”

Section: Introductionmentioning

confidence: 99%

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The empirical comparison of cyclofructans and cyclodextrins as chiral selectors in capillary electrophoretic separation of atropisomers of R,S‐1,1’‐binaphthalene‐2,2’‐diyl hydrogen phosphate

Přibylka

Švidrnoch

Tesařová

et al. 2016

J of Separation Science

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Native cyclofructans and their isopropyl derivatives were studied as chiral selectors in capillary electrophoresis and compared with α- and β-cyclodextrin. R,S-1,1'-Binaphthalene-2,2'-diyl hydrogen phosphate was used as a model chiral compound. The empirical observation of the enantioselectivity of native cyclofructans and isopropyl derivatives of cyclofructans was described and compared with the cyclodextrins. The influence of methanol and acetonitrile, as the most commonly used organic solvents, and sodium dodecyl sulfate as a micelle forming additive on the separation of R,S-1,1'-binaphthalene-2,2'-diyl hydrogen phosphate atropisomers was achieved. The different enantiorecognition abilities resulting from unlike interaction mechanism with R,S-1,1'-binaphthalene-2,2'-diyl hydrogen phosphate were observed for the studied cyclodextrins and cyclofructans, especially when methanol or sodium dodecyl sulfate were used as modifiers of the separation conditions.

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“…The type of the substituent and the degree of substitution have proven to be a determining step in enantiorecognition . On the other hand, the utilization of CFs and their derivatives as CSs in CE is limited, and this is demonstrated by the low number of publications . Native CFs did not demonstrate any significant enantioselectivity, while their derivatives have successfully been applied as CSs in CE .…”

Section: Introductionmentioning

confidence: 99%

Synergistic enantioseparation systems with either cyclodextrins or cyclofructans and L‐alanineTertbutyl ester lactate

et al. 2018

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The combined use of chiral ionic liquids (CILs) and conventional chiral selectors (CSs) in CE, to establish a synergistic system, has proven to be an effective approach for the separation of enantiomeric pairs. In this study, a new CE method was developed, employing a binary system of a CS, either a cyclodextrin (CD) or a cyclofructan (CF), and a chiral amino acid ester‐based ionic liquid (AAIL), for the chiral separation of four basic, acidic and zwitterionic drug compounds. In particular, the enantioseparation of two anticoagulants, warfarin (WAR) and coumachlor (COU), a non‐opioid analgesic, nefopam (NEF) and a third‐generation antihistamine, fexofenadine (FXD), was examined, by supporting the BGE with a CS and the chiral AAIL L‐alanine tert butyl ester lactate (L‐AlaC4Lac). Parameters, such as the type of the CS, the concentration of both the CS and L‐AlaC4Lac, and the BGE pH, were methodically examined in order to optimize the chiral separation of each analyte. It was observed that, in some cases, the addition of the AAIL into the BGE improved both resolution (Rs) and efficiency (N) significantly. In other cases, the synergistic effect enabled baseline separation of analyte enantiomers, at a much lower concentration of the CS. Finally, after optimization of separation conditions, baseline separations (Rs>1.5) of all four analytes were achieved in less than 5 min.

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Isopropyl derivative of cyclofructan 6 as chiral selector in liquid chromatography and capillary electrophoresis

Cited by 23 publications

References 14 publications

Fast separation of enantiomers by capillary electrophoresis using a combination of two capillaries with different internal diameters

Fast separation of enantiomers by capillary electrophoresis using a combination of two capillaries with different internal diameters

The empirical comparison of cyclofructans and cyclodextrins as chiral selectors in capillary electrophoretic separation of atropisomers of R,S‐1,1’‐binaphthalene‐2,2’‐diyl hydrogen phosphate

Synergistic enantioseparation systems with either cyclodextrins or cyclofructans and L‐alanineTertbutyl ester lactate

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