Immobilisation and evaluation of a vancomycin chiral stationary phase for capillary electrochromatography

Wikström, Håkan; Svensson, L.A.; Torstensson, Arne; Owens, Paul K.

doi:10.1016/s0021-9673(99)00874-2

Cited by 107 publications

(69 citation statements)

References 36 publications

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“…In our former work using the same mobile phase [14] we have obtained slightly smaller resolution, R s = 2.5. Wikström et al [15] reported thalidomide enantiomer resolution using the particulate silicabased vancomycin stationary phase in the pure organic Run-to-run reproducibility data are presented in Table 2. From six runs good reproducibility was obtained for retention time, capacity factors and selectivity separating thalidomide enantiomers and DMF as EOF marker.…”

Section: Resultsmentioning

confidence: 99%

“…To convert the diol groups to aldehyde groups, the beds were washed with 60 mM sodium periodate for 2 h at 207C. Later attachment of vancomycin was performed via reductive amination process by washing with vancomycin solution for 24 h at the same temperature [15].…”

Section: Synthesis Of Continuous Bedsmentioning

confidence: 99%

“…Allyl glycidyl ether was used in the comonomer mixture to provide epoxy groups, which later were converted to aldehyde groups. Attachment of vancomycin to the polymeric skeleton was performed via reductive amination [15] of the aldehyde groups on the polymeric skeleton [14]. The task of this study was to simplify the synthesis procedure of the capillary-format nonparticulate vancomycin bed for chiral electrokinetic separations.…”

Section: Introductionmentioning

confidence: 99%

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A simplified synthesis of polymeric nonparticulate stationary phases with macrocyclic antibiotic as chiral selector for capillary electrochromatography

2004

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A simplified approach to synthesize nonparticulate (continuous or monolithic) beds with embedded vancomycin chiral selectors for capillary electrochromatography is proposed. In the present approach, N,N'-diallyltartardiamide monomer with diol functionality is used, which can be readily converted to aldehyde groups via periodate treatment. Parallel to the activation of the polymeric matrix for covalent attachment of vancomycin, the periodate treatment has shown secondary effects on the polymeric bed morphology, namely the increase of the average pore size and porosity of the skeleton. Inversed size-exclusion chromatography was applied to characterize porosimetric properties of the capillary columns before and after the periodate treatment. Electroosmotic and enantioselective properties of the nonparticulate beds synthesized are presented. The approach is of more general interest attaching different affinity groups to the polymeric matrix and/or enhancing the accessibility to the active sites, for instance, in the molecular imprinting technique.

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Section: Resultsmentioning

confidence: 99%

Section: Synthesis Of Continuous Bedsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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A simplified synthesis of polymeric nonparticulate stationary phases with macrocyclic antibiotic as chiral selector for capillary electrochromatography

2004

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“…In a recent work, Wikstrom et al [18] observed that capillaries packed with diol-silica microparticles of 10 mm particle diameter and 1000 Å pore size offered higher efficiency than those packed with particles of 5 mm particle diameter and 100 Å pore size, however, after derivatization with vancomycin, no remarkable difference in the number of theoretical plates (N) was found. Wolf et al [22] used capillaries packed with 3 mm particle diameter and 100 Å pore size derivatized silica with brush-type chiral selectors, achieving theoretical plates as high as 200 000 N/m; they attributed these high values of N to the use of smaller particles packing and to a favorable mass transfer kinetic.…”

Section: Introductionmentioning

confidence: 98%

“…[16]. The same chiral selectors (TE and vancomycin) were also tested in CEC for the separation of mainly basic compounds [9,10,13,[17][18][19][20][21].…”

Section: Introductionmentioning

confidence: 99%

Evaluation of teicoplanin chiral stationary phases of 3.5 and 5 μm inside diameter silica microparticles by polar‐organic mode capillary electrochromatography

et al. 2003

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Different types of fused-silica capillaries of 75 microm inside diameter (ID) were packed, namely type A and B, and evaluated for the direct resolution of racemates of several basic compounds by enantioselective capillary electrochromatography (e-CEC). Type A was packed with a chiral stationary phase (CSP) containing teicoplanin (TE) mixed with silica microparticles (3:1 w/w) while type B contained only the TE-CSP. In both cases, particles of different sizes (3.5 and 5 microm ID) were employed. A polar-organic mobile phase containing methanol-acetonitrile (60-40% v/v and 0.05% w/v ammonium acetate was used. Several beta-blockers (alprenolol, oxprenolol, metoprolol, pindolol, salbutamol, propranolol, atenolol, acebutolol) were baseline-enantioresolved with both capillary types, in very short times.

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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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Immobilisation and evaluation of a vancomycin chiral stationary phase for capillary electrochromatography

Cited by 107 publications

References 36 publications

A simplified synthesis of polymeric nonparticulate stationary phases with macrocyclic antibiotic as chiral selector for capillary electrochromatography

A simplified synthesis of polymeric nonparticulate stationary phases with macrocyclic antibiotic as chiral selector for capillary electrochromatography

Evaluation of teicoplanin chiral stationary phases of 3.5 and 5 μm inside diameter silica microparticles by polar‐organic mode capillary electrochromatography

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

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