Vancomycin capillary electrophoresis

At a pH where vancomycin capillary electrophoresis separations are most effective, at or below its p7 of 7.2, vancomycin is positively charged. This indicates... 

Chu, Y.-H. and Whitesides, G. M., Affinity capillary electrophoresis can simultaneously measure binding constants of multiple peptides to vancomycin,. Org. Chem., 57, 3524, 1992. 

Eanali, S., Desiderio, C., Schulte, G., Heitmeier, S., Strickmann, D., Chankvetadze, B., and Blaschke, G. (1998). Chiral capillary electrophoresis-electrospray mass spectrometry coupling using vancomycin as chiral selector. /. Chromatogr. A 800, 69—76. 

Dunayevskiy, Y.M., Lyubarskaya, Y.V., Chu, Y.-H., Vouros, P., Karger, B.L. Simultaneous measurement of nineteen binding constants of peptides to vancomycin using affinity capillary electrophoresis-mass spectrometry. J. Med. Chem. 1998, 41, 1201-1204. 

YH Chu, LZ Avila, HA Biebuyck, GM Whitesides. Using affinity capillary electrophoresis to identify the peptide in a peptide library that binds most tightly to vancomycin. J Org Chem 58 648-652, 1993. 

J Liu, KJ Volk, MS Lee, M Pucci, S Handwerger. Binding studies of vancomycin to the cytoplasmic peptidoglycan precursors by affinity capillary electrophoresis. Anal Chem 66 2412—2416, 1994. 

F Lynen, Y Zhao, C Becu, F Borremans, P Sandra. Considerations concerning interaction characterization of oligopeptide mixtures with vancomycin using affinity capillary electrophoresis-electrospray mass spectrometry. Electrophoresis 20 2462-2474, 1999. 

Figure 13.9. Affinity capillary electrophoresis-UV-raass spectrometry of a 100-tetrapep-tide library screened for binding to vancomycin (104 fxM in the electrophoresis buffer), (a) The elution of peptides was monitored with UV absorbance during capillary electrophoresis, and the elution time irrieased with increasing affinity for vancomycin. (b) Positive ion electrospray mass spectrum with CID of the Tris adduct of the proton-ated peptide detected at —5 min in the electropherogram shown in a (Reproduced from Ref 52 by permission of the American Chemical ardety.)...

Desiderio, C. Polcaro, C.M. Padiglioni, P. Fanali, S. Enantiomeric separation of acidic herbicides by capillary electrophoresis using vancomycin as chiral selector. J. Chromatogr., A 1997, 781, 503-513. 

Bonnici, P.J. Damen, M. Waterval, J.C.M. Heck, A.J.R. Formation and Efficacy of Vancomycin Group Glycopeptide Antibiotic Stereoisomers Studied by Capillary Electrophoresis and Bioaffinity Mass Spectrometry, Anal. Biochem. 290,292-301 (2001). 

Dunayevskiy, Y.M. Lyubarskaya, Y.V Chu, Y-H. Vouros, R Karger, B.L. Simultaneous Measurement of Nineteen Binding Constants of Peptides to Vancomycin Using Affinity Capillary Electrophoresis-Mass Spectrometry, ... 

To date, the capability of macromolecular peptides as molecular recognition sites has been poorly characterized. Due to the analytical techniques available, first investigations on host-guest complexes were done in the homogeneous phase [55]. One of the most popular cyclic compounds is the depsipeptide, valinomycin, which can complex potassium ions selectively and carry them through lipid membranes [56], Another interesting receptor is the peptide antibiotic, vancomycin [57], This consists of a complicated tricyclic pep-tidic structure and can be used as chiral selector [58] in capillary electrophoresis and HPLC. 

KL Sutton, RM Sutton, AM Stalcup, JA Caruso. A comparison of vancomycin and sulfated beta-cyclodextrin as chiral selectors for enantiomeric separations of selenoamino acids using capillary electrophoresis with UV absorbance detection. Analyst 125 231-234, 2000. 

R Vespalec, HA Billiet, J Frank, P Bocek. Vancomycin as a chiral selector in capillary electrophoresis An appraisal of advantages and limitations. Electrophoresis 17 1214-1221, 1996. 

Vancomycin can be used very effectively as a chiral additive in capillary electrophoresis, but is in some ways inconvenient, as it adsorbs strongly in the UV. However, as low levels of the agent are employed, adequate sensitivity is often realized. Nevertheless, solutes are sometimes detected by fluorescence using an appropriate fluorescing derivative. The separation of the AQC derivative of phenylalanine, methionine and serine is shown in figure 13.9. 

Since first demonstration in 1994 of the potential use of macrocyclic antibiotics as chiral selectors in analysis, glycopeptide antibiotics have been successfully applied for enantiomer separations by liquid chromatography, as recognition components of chiral stationary phases, and by capillary electrophoresis (CE) as soluble chiral selec-tors. Four chiral stationary phases for chromatography with the selectors vancomycin, ristocetin, teicoplanin, and the teicoplanin aglycone are commercialized under the trade name Chirobiotic by Astec and Supelco. Various aspects of analytical applications of glycopeptide antibiotics have been extensively covered in the recent reviews cited above. As an example. Table 2 shows some representative results for CE enantioseparations with vancomycin, ristocetin A, and teicoplanin, which were taken from Ref. 39. 

Fanali S, Desidetio C (1996) Use of vancomycin as chiral selector in capillary electrophoresis. Optimization and quantitation of loxiglumide enantiomers in pharmaceuticals. J High... 

Abstract Medical studies established that vancomycin and other related macro-cyclic antibiotics have an enhanced antimicrobial activity when they are associated as dimers. The carbohydrate units attached to the vancomycin basket have an essential role in the dimerization reaction. Covalently synthesized dimers were found active against vancomycin-resistant bacterial strains. A great similarity between antibiotic potential and enantioselectivity was established. A covalent vancomycin dimer was studied in capillary electrophoresis producing excellent chiral separation of dansyl amino acids. Balhimycin is a macrocyclic glycopeptide stmcturally similar to vancomycin. The small differences are, however, responsible for drastic differences in enantioselectivity in the same experimental conditions. Contributions from studies examining vancomycin s mechanism for antimicrobial activity have substantially aided our understanding of its mechanism in chiral recognition. 

Kang J et al (2004) A mechanistic study of enantiomeric separation with vancomycin and balhimycin as chiral selectors by capillary electrophoresis. Anal Chem 76 2387-2392... 

Desiderio, C., Aturki, Z., and Eanali, S., Use of vancomycin silica stationary phase in packed capillary electrochromatography I. Enantiomer separation of basic compounds. Electrophoresis, 22, 535, 2001. 

Kang, J. W., Van Schepdael, A., Roets, E., and Hoogmartens, J. (2001). Analysis of vancomycin and related impurities by micellar electrokinetic capillary chromatography. Method development and validation. Electrophoresis 22, 2588—2592. 

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