Evaluation of a vancomycin chiral stationary phase in packed capillary supercritical fluid chromatography

Dönnecke, Jürgen; Svensson, L.A.; Gyllenhaal, Olle; Karlsson, K.; Vessman, Jörgen

doi:10.1002/(sici)1520-667x(1999)11:7<521::aid-mcs4>3.0.co;2-n

Cited by 35 publications

(22 citation statements)

References 15 publications

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“…5,6 Additionally, it was found that when these columns were examined in SFC the choice of chromatographic mode was also important. 6 In that study, given the polar nature of both vancomycin and some of the analytes chosen, very high modifier concentrations were occasionally required which resulted in effectively subcritical conditions. It was therefore considered of interest to study this vancomycin CSP in POPLC.…”

Section: Resultsmentioning

confidence: 99%

“…5,6 An LC pump operating at constant pressure was connected to an injector equipped with a 2 ml mobile phase loop followed by a sample injector with an internal loop volume of 0.2 µl. The columns were connected to a UV-detector using a 50 mm I.D.…”

Section: Materials and Methods Instrumentationmentioning

confidence: 99%

“…5,6,16 The diol moieties were oxidized using 20 column volumes of a 60 mM solution of sodium periodate in water/methanol (4+1). After rinsing with water, the immobilization was performed by reductive amination of the resulting aldehyde silica with a 3 mM solution of vancomycin and a threefold excess of sodium cyanoborohydride in 50 mM phosphate buffer pH 7.…”

Section: Column Preparationmentioning

confidence: 97%

“…6 The selectivities are almost identical in SFC. Only the t-butylamino-analog 4 has a clearly lower ␣-value (1.14 compared to 1.24).…”

Section: Comparison With Other Chromatographic Modesmentioning

confidence: 99%

“…[2][3][4][5][6][7][8][9] A number of CSPs can be examined using polar organic mobile phases, but since its introduction for chiral liquid chromatography (LC) with cyclodextrin CSPs in 1988, [10][11][12] only a limited number of reports have appeared. In addition to its application with the cyclodextrin and antibiotic CSPs, the polar organic mobile phase has also been reported in combination with the use of a chiral mobile phase additive on a polygraphitic carbon stationary phase.…”

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confidence: 99%

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Polar organic phase liquid chromatography with packed capillary columns using a vancomycin chiral stationary phase

et al. 2000

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Vancomycin immobilized on silica served as the chiral stationary phase (CSP) in this investigation with polar organic solvents as the mobile phase in liquid chromatography (LC). It was shown that trace amounts of water were beneficial for improving peak shape and efficiency. To regulate the retention and selectivity an acid and/or base were added to the mobile phase where an excess of acid was shown to be preferential for enantioseparation. An unusual increase in selectivity with increasing temperature was shown for the acidic drug, thalidomide. Additionally, nonlinear van't Hoff plots were obtained for metoprolol enantiomers that showed increased retention with increasing temperature. Metoprolol also showed unusual behavior in the polar organic phase when water was added to resemble reversed-phase chromatography, with minimum retention observed at high water or high methanol concentrations. In both instances a high degree of electrostatic interaction between metoprolol and vancomycin was concluded. Metoprolol and ten of its analogs were examined on this CSP to evaluate the enantiorecognition process. A comparison in enantioselectivity for a number of acidic and basic drugs using this CSP was also carried out using the polar organic phase, reversed phase, and normal phase LC which were all compared to the results obtained in supercritical fluid chromatography (SFC). Polar organic phase LC offered a better separation of basic molecules while reversed phase LC was preferred for the resolution of acids. SFC showed the broadest enantioselectivity overall and normal phase LC indicated similar properties, as expected, to SFC but with lower column efficiency. Copyright 2000 Wiley-Liss, Inc.

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Section: Resultsmentioning

confidence: 99%

Section: Materials and Methods Instrumentationmentioning

confidence: 99%

Section: Column Preparationmentioning

confidence: 97%

“…6 The selectivities are almost identical in SFC. Only the t-butylamino-analog 4 has a clearly lower ␣-value (1.14 compared to 1.24).…”

Section: Comparison With Other Chromatographic Modesmentioning

confidence: 99%

mentioning

confidence: 99%

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Polar organic phase liquid chromatography with packed capillary columns using a vancomycin chiral stationary phase

et al. 2000

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Use of vancomycin silica stationary phase in packed capillary electrochromatography I. Enantiomer separation of basic compounds

2001

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Chiral separation of basic compounds was achieved by using 75 or 100 microm ID fused-silica capillaries packed with a vanoomycin-modified diol silica stationary phase. The capillary was firstly packed for about 12 cm with a slurry mixture composed of diolsilica (3:1) then with the vancomycin modified diol-silica (3:1) (23 cm), and finally with diol-silica (3:1) for about 2 cm. Frits were prepared by a heating wire at the two ends of the capillary; the detector window was prepared at 8.5 cm from the end of the capillary where vancomycin was not present. The influence of the mobile phase composition (pH and concentration, organic modifier type and concentration) on the velocity of the electroosmotic flow, chiral resolution and enantioselectivity was studied. Good enantiomeric resolution was achieved for atenolol, oxprenolol, propranolol, and venlafaxine using a mobile phase composition of 100 mM ammonium acetate solution (pH 6)/water/acetonitrile (5:5:90 v/v/v) while for terbutaline a mixture of 5:15:80 v/v/v provided the best separations. The use of methanol instead of acetonitrile caused a general increase of enantiomer resolution of the studied compounds together with a reduction of efficiency and detector response. However, the combination of acetonitrile and methanol in the mobile phase (as, e.g., 10% methanol and 80% acetonitrile) allowed to improve the enantiomer resolution with satisfactory detector response.

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Macrocyclic glycopeptide‐based chiral selectors for enantioseparation in sub/supercritical fluid chromatography

Folprechtová

Kalíková

2020

Analytical Science Advances

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Increasing number of reported works dealing with macrocyclic glycopeptide‐based columns in sub/supercritical fluid chromatography (SFC) points to the growing interest in this area. With the development and production of sub 2 µm fully porous particles and superficially porous particles with bonded macrocyclic glycopeptides, significant improvements have been made in ultrafast high efficiency chiral SFC. This review article gives an overview of macrocyclic glycopeptide‐based chiral selectors that were used in theoretical studies and/or applications in SFC. The review covers the period from 1997 when macrocyclic glycopeptides were first used in SFC till the end of July 2020 according to Web of Science. This work can also be helpful to analysts searching for an appropriate method for the separation/determination of enantiomers of their interest.

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Evaluation of a vancomycin chiral stationary phase in packed capillary supercritical fluid chromatography

Cited by 35 publications

References 15 publications

Polar organic phase liquid chromatography with packed capillary columns using a vancomycin chiral stationary phase

Polar organic phase liquid chromatography with packed capillary columns using a vancomycin chiral stationary phase

Use of vancomycin silica stationary phase in packed capillary electrochromatography I. Enantiomer separation of basic compounds

Macrocyclic glycopeptide‐based chiral selectors for enantioseparation in sub/supercritical fluid chromatography

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