Chiral separation on achiral stationary phases with different functionalities using β-cyclodextrin in the mobile phase and application to bioanalysis and coupled columns

Walhagen, Agneta; Edholm, L. E.

doi:10.1007/bf02276243

Cited by 43 publications

(14 citation statements)

References 35 publications

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“…The role of the achiral stationary phases has been investigated with cyclodextrins as chiral mobile-phase additives, but some contradictory results have been described in the literature. [36][37][38] Therefore, we wanted to examine also the effect of the stationary-phase structure on retention and enantioseparation of the profen NSAIDs in this work. Based on the preliminary results, MeOH-0.1% TEAA buffer, pH 5.0 in the volume ratio of 50:50 was selected as suitable mobile phase, to which vancomycin was added.…”

Section: Results and Discussion Enantioselective Separations Of Profementioning

confidence: 99%

“…35 The aim of this study was to evaluate the chromatographic behavior of two direct cLC approaches for the enantioseparation of chiral drugs, fenoprofen, carprofen, flurbiprofen, indoprofen, flobufen, ketoprofen, and suprofen. As the role of the achiral stationary phase in the enantioselective separation systems is not always clearly interpreted, [36][37][38] two capillary columns, Nucleosil 100 C8 HD and Nucleosil 100 C18 HD, were investigated with vancomycin added to the mobile phase. The second way of direct separation was vancomycin CSP Chirobiotic V and achiral mobile phase.…”

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Vancomycin as chiral selector for enantioselective separation of selected profen nonsteroidal anti‐inflammatory drugs incapillary liquid chromatography

et al. 2006

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The chiral selector vancomycin was used either as mobile phase additive or bound as a chiral stationary phase (CSP) for the stereoselective separation of seven racemic nonsteroidal anti-inflammatory drugs (NSAIDs), fenoprofen, carprofen, flurbiprofen, indoprofen, flobufen, ketoprofen, and suprofen, by capillary liquid chromatography. The effect of the type of stationary phase, the chiral column Chirobiotic V or the achiral stationary phases Nucleosil 100 C8 HD and Nucleosil 100 C18 HD, and the concentration of vancomycin in the mobile phase on separation of the drug enantiomers were evaluated. All the drugs, except flobufen, were successfully enantioseparated on Nucleosil 100 C8 HD with 4 mM vancomycin present in the mobile phase (composed of methanol and buffer) in the reversed phase mode. On the vancomycin-bonded chiral stationary phase, it was difficult to get enantioseparations of the profen NSAIDs. However, flobufen gave better enantioseparation on the vancomycin CSP. The better enantioresolution of the majority of profen derivatives on the achiral columns with vancomycin added to the mobile phase can be attributed in particular to the higher separation efficiency of this capillary chromatographic system. In addition, vancomycin dimers, formed in the mobile phase, seem to offer a better steric arrangement for stereoselective interaction to these analytes than the vancomycin bonded on the CSP. These substantial differences in the CS structure significantly influence the chiral discrimination mechanism.

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Section: Results and Discussion Enantioselective Separations Of Profementioning

confidence: 99%

mentioning

confidence: 99%

Vancomycin as chiral selector for enantioselective separation of selected profen nonsteroidal anti‐inflammatory drugs incapillary liquid chromatography

et al. 2006

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“…To minimize the cost, packed-fused-silica capillary columns were employed in some cases (Han and Armstrong, 1987;Wannman et al, 1992). Because of the low flow rate in these microcolumns, only minimal amounts of CD are required.…”

Section: Cyclodextrin Mobile Phase Additivesmentioning

confidence: 99%

Direct enantiomeric separations by high performance liquid chromatography using cyclodextrins

Han

1997

Biomed. Chromatogr.

100

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“…A baseline separation of oxazepam enantiomers has been obtained on a CSP of b-cyclodextrin bonded to a polymer gel while only partial resolution has resulted for lorazepam [18]. An alternative approach has been represented by the addition of b-cyclodextrin or its derivatives to a mobile phase [22,23]. Various types of achiral stationary phases used in a reverse-phase mode with the CD chiral additives in the mobile phase have affected retention but their influence on enantioresolution of oxazepam, lorazepam, and some other drugs has been almost negligible.…”

Section: Introductionmentioning

confidence: 99%

Comparison of enantioseparation of selected benzodiazepine and phenothiazine derivatives on chiral stationary phases based on β‐cyclodextrin and macrocyclic antibiotics

Tesařová¹,

Bosáková

2003

J of Separation Science

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Comparison of enantioseparation of selected benzodiazepine and phenothiazine derivatives on chiral stationary phases based on b-cyclodextrin and macrocyclic antibiotics Enantioselective separation of some phenothiazine and benzodiazepine derivatives was studied on six different chiral stationary phases (CSPs) in HPLC. Selected CSPs, with respect to the structure of the separated compounds, were either based on b-cyclodextrin chiral selectors -underivatized b-cyclodextrin and hydroxypropyl ether b-cyclodextrin, or on macrocyclic antibiotics -vancomycin, teicoplanin, teicoplanin aglycone, and ristocetin A. Measurements were carried out in a reversedphase separation mode. The influence of mobile phase composition on retention and enantioseparation was studied. Benzodiazepines could be enantioresolved with almost all the chiral stationary phases used, except for the vancomycin-bonded CSP. Peak coalescence of oxazepam and lorazepam was observed if separation was carried out at laboratory temperature. Reduced temperature was required in some instances in order to avoid the on-column racemization. Separation systems composed of teicoplanin-bonded CSP and buffer-methanolic or pure methanolic mobile phases were shown to be suitable even for preparative purposes due to high resolution values of the enantiomers. Enantioseparation of phenothiazine derivatives was more difficult to achieve but it was successful, at least partly, also with both types of the CSPs used (except for levomepromazine).

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Chiral separation on achiral stationary phases with different functionalities using β-cyclodextrin in the mobile phase and application to bioanalysis and coupled columns

Cited by 43 publications

References 35 publications

Vancomycin as chiral selector for enantioselective separation of selected profen nonsteroidal anti‐inflammatory drugs incapillary liquid chromatography

Vancomycin as chiral selector for enantioselective separation of selected profen nonsteroidal anti‐inflammatory drugs incapillary liquid chromatography

Direct enantiomeric separations by high performance liquid chromatography using cyclodextrins

Comparison of enantioseparation of selected benzodiazepine and phenothiazine derivatives on chiral stationary phases based on β‐cyclodextrin and macrocyclic antibiotics

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