Enantiomeric HPLC Separation of Selected Chiral Drugs Using Native and Derivatized β-Cyclodextrins as Chiral Mobile Phase Additives

Ameyibor, Emmanuel; Stewart, James T.

doi:10.1080/10826079708013658

Cited by 52 publications

(29 citation statements)

References 14 publications

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“…3-5 1) derivatization of the analytes with chiral reagents to form resolvable diastereomeric derivatives; 3,6 2) development of chiral additives in the mobile phase; 3,7,8 and 3) development of chiral stationary phase.…”

mentioning

confidence: 99%

Simultaneous analysis of enantiomeric composition of amino acids and N‐acetyl‐amino acids by enantioselective chromatography

2001

Chirality

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Among the three chiral columns, CHIROBIOTIC T, CHIRLPAK WH, and CHIRALCEL OD-R, tested for the separation of racemic amino acids and N-acetyl-amino acids, only CHIROBIOTIC T chiral column which is based on covalently bonded amphoteric glycopeptide, teicoplanin, as the stationary phase ligand could be successfully developed to enantiomerically separate racemic amino acids and N-acetyl amino acids simultaneously. This method can be used to determine the enantiomeric composition of amino acids and N-acetyl-amino acids in the catalysis of D-aminoacylase or L-aminoacylase and the conversion rate of N-acylamino acid racemases.

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mentioning

confidence: 99%

Simultaneous analysis of enantiomeric composition of amino acids and N‐acetyl‐amino acids by enantioselective chromatography

2001

Chirality

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“…Ameyibor and Stewart [2] have reported that the interactions between the interior of the cyclodextrin cavity and the portion of the analyte inside the cavity were constituted of attractive hydrophobic, van der Waals, hydrogen bonding and dipole-dipole interactions. The functional groups on the rim of cyclodextrin (primary and secondary hydroxyl groups) and the portion of the analyte outside the cavity must take place for chiral recognition to occur.…”

Section: Chiral Recognitionmentioning

confidence: 99%

“…Pullen et al [1] found [3-CD to be a useful mobile phase additive for the separation of two racemic cycloheptaindole derivatives using the bare silica stationary phase. Ameyibor and Stewart [2] observed that increasing the ~-CD or hydroxypropyl-13-CD (HP-13-CD) concentrations in the mobile phase resulted in an increase in resolution of the enantiomers of lorazepam, temazepam, oxazepam, chlorthalidone, trimeprazine, trimipramine, ketoprofen and fenoprofen. Then, the resolution reached a plateau region and decreased when the cyclodextrin concentration increased.…”

Section: Introductionmentioning

confidence: 99%

A simple model for RPLC retention and selectivity of imidazole enantiomers using β-cyclodextrin as chiral selector

1998

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SummaryUsing reversed phase liquid chromatography (RPLC), this paper investigates the enantioselectivity variations, in a series of weak polar R, S-imidazole derivatives, with [3-cyclodextrin concentration in the mobile phase over a wide range of column temperatures. These compounds are used for the treatment of onychomycosis. The selectivity data obtained were assessed using a chiral recognition model, based on the formation of complexes between the solute molecule and the cyclodextrin cavity. Gibbs Helmholtz parameters (A(AH), A(AS)) between R-and S-enantiomers were determined from the logarithm of the separation factor, or, versus the reciprocal of the temperature plots. The thermodynamic results predicted that the enantioselectivity mechanism was related to both the solute's bulkiness and the asymmetric carbon atom configuration.

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“…32 Only a few studies employed chiral mobilephase additives (mostly cyclodextrin chiral selectors) for enantioseparation of profen NSAIDs in HPLC. 33,34 Successful enantioseparations of ketoprofen and fenoprofen were obtained only with hydroxypropyl b-cyclodextrin. 33 Improved chiral selectivity was reported for flurbiprofen on the Chirobiotic V column after addition of vancomycin to the mobile phase.…”

mentioning

confidence: 99%

“…33,34 Successful enantioseparations of ketoprofen and fenoprofen were obtained only with hydroxypropyl b-cyclodextrin. 33 Improved chiral selectivity was reported for flurbiprofen on the Chirobiotic V column after addition of vancomycin to the mobile phase. 17 The capillary liquid chromatography technique has not yet been employed for chiral separation of profens.…”

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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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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Enantiomeric HPLC Separation of Selected Chiral Drugs Using Native and Derivatized β-Cyclodextrins as Chiral Mobile Phase Additives

Cited by 52 publications

References 14 publications

Simultaneous analysis of enantiomeric composition of amino acids and N‐acetyl‐amino acids by enantioselective chromatography

Simultaneous analysis of enantiomeric composition of amino acids and N‐acetyl‐amino acids by enantioselective chromatography

A simple model for RPLC retention and selectivity of imidazole enantiomers using β-cyclodextrin as chiral selector

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

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