High-performance liquid chromatographic and capillary electrophoretic enantioseparation of plant growth regulators and related indole compounds using macrocyclic antibiotics as chiral selectors

Hui, F.; Ekborg-Ott, K. Helen; Armstrong, D. W.

doi:10.1016/s0021-9673(00)00954-7

Cited by 42 publications

(19 citation statements)

References 11 publications

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“…Armstrong and co-workers [147,148] have reported that the addition of small amounts of different organic solvents (i.e., methanol, ethanol, and acetonitrile) in the run buffer is capable of improving the analyte resolution when using surface-active macrocyclic antibiotics as chiral selectors, such as rifamycin B, avoparin and teicoplanin, which are known to form micelles above their CMC. The improved resolution can be attributed to a decrease in aggregation of these surfactant-like antibiotics, which has been postulated to hinder enantioselectivity.…”

Section: Optical Isomersmentioning

confidence: 99%

Effects of organic solvents on sample pretreatment and separation performances in capillary electrophoresis

Huie

2003

Electrophoresis

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A review of recent developments in theoretical as well as application studies concerning the use of organic solvents, either as purely nonaqueous solvents, hydro-organic mixtures, or a combination of an organic solvent with another organic modifier(s), in the sample matrix and/or separation buffer for effecting sample pretreatment and/or improving separation performances in capillary electrophoresis (CE) is presented. In particular, recent advances made in furthering the basic understanding of selectivity changes that occur in capillary zone electrophoresis due the presence of organic solvents in the separation medium, based on in-depth studies of fundamental processes, such as acid-base chemistry, ion-ion and ion-solvent interactions, were discussed in detail. The utilization of organic solvents for improving the resolution of highly challenging and important separations, i.e., those involving the separation of positional and optical isomers, was also critically reviewed. Furthermore, a comprehensive survey of the use of organic solvents for on-line sample pretreatment, e.g., minimizing aggregation and maximizing solubilization of hydrophobic analytes, improving concentration detection sensitivity for analytes via the use of sample stacking, was presented and discussed. Moreover, recent applications involving the use of organic solvents for improving the CE separations of a variety of molecular species with significance in various disciplines, including biological, environmental and pharmaceutical areas, were summarized and tabulated.

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Section: Optical Isomersmentioning

confidence: 99%

Effects of organic solvents on sample pretreatment and separation performances in capillary electrophoresis

Huie

2003

Electrophoresis

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“…This antibiotic was first introduced as chiral selector in HPLC by Armstrong and coworkers [22]. There are a large of number of reports dealing with the use of vancomycin for chiral resolution either covalently bonded to stationary phases using HPLC [23,24], nanoLC [25], and CEC [26 -28] or added to the background electrolyte (BGE) employing CZE [29 -31].…”

Section: Introductionmentioning

confidence: 99%

Enantiomeric separation of mirtazapine and its metabolites by nano‐liquid chromatography with UV‐absorption and mass spectrometric detection

Fanali¹,

Aturki

Kaicka

et al. 2005

J of Separation Science

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Mirtazapine (MIR) and two of its main metabolites, namely, 8-hydroxymirtazapine and N-desmethylmirtazapine, were separated in totheir enantiomers by nanoLC in a laboratory-made fused-silica capillary column (75 microm ID) packed with a vancomycin-modified silica stationary phase. The simultaneous separation of the three couples of the studied enantiomers was achieved in less than 33 min, using an experimentally optimized mobile phase delivered in the isocratic mode. Optimization of the mobile-phase composition was achieved by testing the influence of the buffer pH and concentration, the water concentration, the organic modifier type and concentration, and on the retention and resolution of the analytes. The optimum mobile-phase composition contained 500 mM ammonium acetate pH 4.5/water/MeOH/MeCN, 1:14:40:45 v/v/v/v. Using a UV detector at 205 nm, the method was validated studying several experimental parameters such as LOD and LOQ, intraday and interday repeatability, and linearity. Good results were achieved: LOD and LOQ were in the range 5-15 and 10-40 microg/mL, respectively (the highest value was obtained for the DEMIR enantiomers); correlation coefficients, 0.9993-0.9999; the intraday and interday precision was acceptable (RSD < 2%) using an internal standard. The method was tested for the separation of the studied enantiomers in an extracted (solid-phase) serum sample spiked with standard racemic mixture of MIR and its two metabolites. Finally, the nanoLC system was connected to a mass spectrometer through a nanoelectrospray interface and the MS, MS2, and MS3 spectra were acquired showing the potential of the system used for characterization and identification of the separated analytes.

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“…It is interesting to note that the enantioseparation of acidic compounds ketoprofen and suprofen (which are structurally different from DALAA) are also enhanced by the use of A82846B. This is possibly due to the carboxylate group being the principal docking site between analytes and macrocyclic glycopeptides 23 and hence promoting formation of the dimer.…”

Section: A82846b In Comparison With Vancomycin As a Mobilementioning

confidence: 99%

Link between biological signaling and increased enantioseparations of acids using glycopeptide antibiotics

2003

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The vancomycin analog A82846B has been shown to provide excellent selectivity as a chiral recognition agent for some acidic test analytes in capillary electrophoresis (CE) and high-performance liquid chromatography (HPLC). In both modes A82846B outperforms vancomycin as a chiral selector. A82846B has enhanced antibacterial activity data in comparison to vancomycin, which is probably due to the increased dimerization constant of over 100 in magnitude in comparison to vancomycin. The link between the electrophoretic and chromatographic separations observed and the biological activity of A82846B is discussed. Dimerization of A82846B in solution was proposed as a theory as to why A82846B gave such enhanced separations for acidic racemates. Further literature and experimental studies support the theory.

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High-performance liquid chromatographic and capillary electrophoretic enantioseparation of plant growth regulators and related indole compounds using macrocyclic antibiotics as chiral selectors

Cited by 42 publications

References 11 publications

Effects of organic solvents on sample pretreatment and separation performances in capillary electrophoresis

Effects of organic solvents on sample pretreatment and separation performances in capillary electrophoresis

Enantiomeric separation of mirtazapine and its metabolites by nano‐liquid chromatography with UV‐absorption and mass spectrometric detection

Link between biological signaling and increased enantioseparations of acids using glycopeptide antibiotics

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