Enantioseparation of glutethimide and its 5‐OH‐metabolite in capillary electrophoresis and study of selector‐selectand interactions using one‐dimensional rotating frame nuclear Overhauser and exchange spectroscopy

Chankvetadze, Bezhan; Burjanadze, Naira; Bergander, Klaus; Blaschke, Gottfried

doi:10.1002/1522-2683(200206)23:12<1906::aid-elps1906>3.0.co;2-#

Electrophoresis

2002

DOI: 10.1002/1522-2683(200206)23:12<1906::aid-elps1906>3.0.co;2-#

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Enantioseparation of glutethimide and its 5‐OH‐metabolite in capillary electrophoresis and study of selector‐selectand interactions using one‐dimensional rotating frame nuclear Overhauser and exchange spectroscopy

Bezhan Chankvetadze

Naira Burjanadze

Klaus Bergander

et al.

Abstract: Enantioseparation of glutethimide (GT) and its 5-hydroxy metabolite (5-OH-GT) has been studied with several charged cyclodextrin (CD) derivatives. The emphasis was made on the enantiomer migration order of GT and simultaneous enantioseparation of GT and 5-OH-GT. The possible structural differences of GT complexes with three different single isomer charged CD derivatives were studied using one-dimensional rotating frame nuclear Overhauser and exchange spectroscopy (1-D ROESY).

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Cited by 3 publications

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Simultaneous enantioseparation and sensitive detection of eight β‐blockers using capillary electrochromatography‐electrospray ionization‐mass spectrometry

Zheng

Shamsi

2006

Electrophoresis

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The feasibility of using vancomycin chiral stationary phase (CSP) and polar organic eluent is investigated for simultaneous enantioseparation of eight beta-blockers using CEC coupled to ESI mass spectrometric detection (ESI-MS). The internally tapered capillaries were utilized to pack CEC-MS columns. As compared to externally tapered columns, the use of internally tapered columns demonstrated enhanced stability, durability, and reproducibility. A mixture containing methanol/ACN/acetic acid/triethylamine at 70:30:1.6:0.2 v/v/v/v was considered as optimum mobile phase since it provided a good compromise between resolution and analysis time. As expected, sheath liquid and ESI-MS parameters mainly influenced the detection sensitivity. Interestingly, structural information of beta-blockers was available by varying the MS fragmentor voltage using in-house CID in the scan mode. In order to maximize the chiral/achiral resolution, various column-coupling approaches using teicoplanin as complementary CSP to vancomycin were tested. Several changes in the elution order of beta-blockers were observed using multimodal CSPs with some improvement in chiral or achiral resolution. The quantitative aspects of the CEC-MS method were demonstrated using R- and S-talinolol as internal standards. The calibration curves of beta-blockers showed good linearity in the range of 3-600 microM. The enantiomer of beta-blockers at a concentration of 30 nM was detectable. Furthermore, both 0.1 and 1% of the S-enantiomer could be precisely quantified in the presence of 99.9 and 99% of the R-isomer of beta-blocker.

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Simultaneous enantioseparation and sensitive detection of eight β‐blockers using capillary electrochromatography‐electrospray ionization‐mass spectrometry

Zheng

Shamsi

2006

Electrophoresis

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Optimized separation of β-blockers with multiple chiral centers using capillary electrochromatography–mass spectrometry☆

Bragg

Norton

Shamsi

2008

Journal of Chromatography B

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This work focuses on the simultaneous analysis of β-blockers with multiple stereogenic centers using capillary electrochromatography–mass spectrometry (CEC–MS) with a vancomycin stationary phase. The critical mobile phase variables (composition of organic solvents, acid/base ratios) as well as column temperature and electric field strength, effecting enantioresolution and analysis time were first optimized sequentially. Next, to achieve global optimum a multivariate D-optimal design was used. Although multivariate approach did not improve enantioresolution any further, analysis time was significantly reduced. Under optimum CEC–MS conditions, all stereoisomers were resolved with resolution in the range 1.0−3.1 in less than 60 min with an average signal-to-noise (S/N) greater than 1000. The developed CEC–MS method has the potential to emerge as a screening method for analysis of multiple chiral compounds using a single protocol using the same column and mobile phase conditions, thus reducing the operation time and cost.

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Combined approach using capillary electrophoresis and NMR spectroscopy for an understanding of enantioselective recognition mechanisms by cyclodextrins

2004

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This tutorial review describes the contribution of chiral capillary electrophoresis in combination with other instrumental techniques, especially nuclear magnetic resonance spectroscopy, to a better understanding of the chiral recognition mechanisms by cyclodextrins. Aspects such as affinity pattern of enantiomers towards various cyclodextrins as well as the stoichiometry of the resulting complexes, the equilibrium constants and the structure of complexes are addressed. In addition to the aforementioned techniques, the usefulness of complementary instrumental and molecular modeling techniques for an understanding of the chiral recognition mechanisms of cyclodextrins is also illustrated.

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Enantioseparation of glutethimide and its 5‐OH‐metabolite in capillary electrophoresis and study of selector‐selectand interactions using one‐dimensional rotating frame nuclear Overhauser and exchange spectroscopy

Cited by 3 publications

References 18 publications

Simultaneous enantioseparation and sensitive detection of eight β‐blockers using capillary electrochromatography‐electrospray ionization‐mass spectrometry

Simultaneous enantioseparation and sensitive detection of eight β‐blockers using capillary electrochromatography‐electrospray ionization‐mass spectrometry

Optimized separation of β-blockers with multiple chiral centers using capillary electrochromatography–mass spectrometry☆

Combined approach using capillary electrophoresis and NMR spectroscopy for an understanding of enantioselective recognition mechanisms by cyclodextrins

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