Avoparcin, a new macrocyclic antibiotic chiral run buffer additive for capillary electrophoresis

Abstract

Avoparcin, like vancomycin, teicoplanin, and ristocetin A, belongs to the family of macrocyclic glycopeptide antibiotics. These antibiotics have all been used as effective chiral selectors for capillary electrophoresis (CE), thin-layer chromatography (TLC), and high performance liquid chromatography (HPLC). The present work focuses on avoparcin, which has been shown to be an excellent chiral selector for the CE enantioseparation of many N-blocked amino acids, as well as several anti-inflammatory drugs of pharmaceutical importance. The use of avoparcin as a chiral run buffer additive in CE is discussed, as well as the effects of changing experimental parameters, like avoparcin concentration, pH, organic modifiers, etc. Comparisons of enantioseparations of some N-3,5-dinitrobenzoyl-derivatized amino acids, using either avoparcin, ristocetin A, teicoplanin, or vancomycin in the run buffer, are also made. In general, vancomycin had the longest migration times, and ristocetin A the shortest, while avoparcin was intermediate. Generally, at least one of the four chiral selectors produced an excellent separation, while a different macrocyclic antibiotic produced a poor separation. Currently, we see no way to predict which chiral run buffer additive will be best or worst for an individual solute.

Application of antibiotics as chiral selectors for capillary electrophoretic enantioseparation of pharmaceuticals: a review

“…To remove the adsorbed antibiotics from the untreated capillary walls, an intense and longer washing procedure using water–antibiotics free BGE and NaOH (0.01 m ) has been recommended (Ekborg‐Ott et al ., ; Vespalec et al ., ).…”

Chiral Separations by Capillary Electrophoresis

“…Also, new types of selectors were developed over the years. For example, Armstrong's group [100] proposed avoparcin as a new chiral selector for electrophoretic separations. It was tested for the separation of 59 analytes, including N -3,5-dinitrobenzoyl derivatives of amino acids, some NSAIDs, and dansylphenylalanine and other compounds.…”

Recent developments in chiral capillary electrophoresis and applications of this technique to pharmaceutical and biomedical analysis

“…Macrocyclic antibiotics such as vancomycin and teicoplanin are effective chiral selectors for acidic analytes, whereas rifampycins can recognize basic enantiomers. Recently avoparcin as a new macrocyclic antibiotic has been applied for enantioseparation of N-derivatized amino acids and anti-inflammatory drugs [215]. Avoparcin like vancomycin belongs to the family of macrocyclic glycopeptide antibiotic.…”