Evaluation of the macrocyclic antibiotic vancomycin as a chiral selector for capillary electrophoresis

Armstrong, Daniel W.; Rundlett, Kimber L.; Chen, Jing‐Ran ‐R

doi:10.1002/chir.530060609

Cited by 298 publications

(229 citation statements)

References 9 publications

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“…Macrocyclic antibiotics as chiral selectors were introduced by Armstrong [397]. Three classes of antibiotics have been introduced as chiral selectors: Ansamycins such as rifamycin B, rifamycin SV; the glycopeptides vancomycin, ristocetin and teicoplanin introduced by Armstrong [397] and the aminoglucoside antibiotics streptomycin, fradiomycin and kanamycin investigated by Nishi et al [385].…”

Section: Neutral CD Derivatives a Great Variety Of Neutral Derivativmentioning

confidence: 99%

Chiral separation by chromatographic and electromigration techniques. A Review

Gübitz

Schmid

2001

Biopharm & Drug Disp

225

135

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This review gives a survey of different chiral separation principles and their use in high-performance liquid chromatography (HPLC), gas chromatography (GC), supercritical fluid chromatography (SFC), thin-layer chromatography (TLC), capillary electrophoresis (CE) and capillary electrochromatography (CEC) highlighting new developments and innovative techniques. The mechanisms of the different separation principles are briefly discussed and some selected applications are shown.

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Section: Neutral CD Derivatives a Great Variety Of Neutral Derivativmentioning

confidence: 99%

Chiral separation by chromatographic and electromigration techniques. A Review

Gübitz

Schmid

2001

Biopharm & Drug Disp

225

135

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“…Approximately 500 racemic analytes have been electrophoretically resolved with glycopeptide antibiotics, including most N-blocked amino acids, numerous nonsteroidal antiinflammatory compounds, antineoplasics, lactic acids, herbicides, rodenticides and a variety of pharmaceutically important compounds [15,17,18,21,22,28]. Resolution values between 10 and 20 are not uncommon.…”

Section: Applicationsmentioning

confidence: 99%

“…Macrocyclic antibiotics are the newest class of chiral selectors recently introduced by Armstrong and co-workers [11][12][13][14][15][16][17][18][19][20][21][22][23][24]27,30]. More enantiomers were resolved with these selectors in CE than with any other class of chiral additives in the past few years.…”

Section: Introductionmentioning

confidence: 99%

Enantioseparation in CE using macrocyclic antibiotics as chiral selectors

Hui¹,

Caude²

1999

Analusis

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Micellar phaseA mixed micelle system is obtained by adding surfactants such as SDS (sodium dodecylsulfate) above its critical micelle concentration (CMC) to the run buffers containing antibiotics. To date, only the glycopeptide antibiotics have been used in conjunction with micelles. In the case of vancomycin, it is estimated that approximately 90 % of vancomycin is bound to the SDS micelle. Thus there are three pseudophases: the free vancomycin, the vancomycin-SDS mixed micelle and the bulk aqueous solution. The use of such mixed micelle systems allow the resolution a variety of hydrophobic, neutral analytes, e.g., pesticides and drugs [16]. The major separation mechanism is thought to be the partitioning of hydrophobic, neutral compounds between the three pseudophases. In a recent study, Rundlett and Armstrong [17] found the addition of SDS micelles with vancomycin to the run buffer can reverse the elution order of enantiomers, decreases analysis times and enhances efficiencies by one order of magnitude.The addition of SDS to a teicoplanin-based separation produces similar effects to vancomycin experiments [17,22]. However, the elution order of enantiomers in teicoplanin system is not universal. In the case of ristocetin A, the addition of SDS to the analogous conditions does not produce the extensive increase in efficiency and decrease in migration times. Furthermore, there is a significant concentrationdependent effect on selectivity and the reversal of elution order is uncommon [21]. Complementarity among glycopeptide antibiotics used as chiral selectorsAlthough all of three glycopeptide antibiotics vancomycin, teicoplanin and ristocetin A belong to the same family, they have some distinct structural differences as well. Therefore, they exhibit somewhat similar but not identical enantioselectivities. In fact, the glycopeptide antibiotics are complementary to one another. Armstrong et al. proposed that if only a partial enantioresolution can be obtained with one glycopeptide, there is a high probability that a baseline or better separation may be obtained with another glycopeptide [30]. This "principle of complementary separations" is illustrated in figure 3. While it is not yet possible to predict which glycopeptide antibiotic will provide the best resolution for a given analyte, it appears that a partial resolution with one selector usually can be improved upon by using one of the structurally related macrocyclic glycopeptide chiral selectors. ApplicationsGenerally, rifamycin B is chosen to separate cationic compounds [12,26], while the glycopeptide antibiotics vancomycin, teicoplanin and ristocetin A are used for the separation of compounds containing an anionic moiety such as carboxylate, phosphate, sulphonate groups, etc. Approximately 500 racemic analytes have been electrophoretically resolved with glycopeptide antibiotics, including most N-blocked amino acids, numerous nonsteroidal antiinflammatory compounds, antineoplasics, lactic acids, herbicides, rodenticides and a variety of pharmaceutically im...

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“…Chemically bonded antibiotics, e.g., vancomycin, ristocetin A, rifamycin [102] and teicoplanin [103], can be used as efficient stationary phases for enantioseparations of amino acids and peptides. Simple mobile phases, usually aqueous ethanol, are used.…”

Section: Chiral Separationsmentioning

confidence: 99%

Stationary phases for peptide analysis by high performance liquid chromatography: a review

Štulı́k¹,

Pacáková²,

Suchánková³

et al. 1997

Analytica Chimica Acta

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A survey is given of modern stationary phases employed in high performance liquid chromatography (HPLC) analysis of peptides. The physico-chemical properties of peptides and their consequences for the selection and optimization of the separation system are briefly discussed, followed by a summary of the approaches to the selection and characterization of stationary phases. The properties and applicability of various stationary phases are then critically reviewed, including aspects such as size-exclusion, ion-exchange, reversed-phase, hydrophobic-interaction, affinity and chiral systems, as well as some specialized separation techniques. Emphasis is placed on the most recent literature. 0 1997 Elsevier Science B.V.

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Evaluation of the macrocyclic antibiotic vancomycin as a chiral selector for capillary electrophoresis

Cited by 298 publications

References 9 publications

Chiral separation by chromatographic and electromigration techniques. A Review

Chiral separation by chromatographic and electromigration techniques. A Review

Enantioseparation in CE using macrocyclic antibiotics as chiral selectors

Stationary phases for peptide analysis by high performance liquid chromatography: a review

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