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Capillary electrophoretic enantiomeric separations using the glycopeptide antibiotic, teicoplanin
Author(s) -
Rundlett Kimber L.,
Gasper Mary P.,
Zhou Eve Y.,
Armstrong Daniel W.
Publication year - 1996
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/(sici)1520-636x(1996)8:1<88::aid-chir15>3.0.co;2-o
Subject(s) - teicoplanin , chemistry , glycopeptide , capillary electrophoresis , enantiomer , glycopeptide antibiotic , chromatography , micelle , cationic polymerization , aqueous solution , combinatorial chemistry , organic chemistry , antibiotics , vancomycin , bacteria , biochemistry , biology , genetics , staphylococcus aureus
Teicoplanin is the third in a series of macrocyclic glycopeptide antibiotics that has been evaluated as a chiral selector in capillary electrophoresis (CE). It was used to resolve over 100 anionic racemates at low selector concentrations. Like the other related glycopeptide antibiotics, its enantioselectivity tends to be opposite to that of the ansa‐type antibiotics which prefers cationic compounds, particularly amines. Factors that affect teicoplanin‐based enantioseparations include the selector concentration, pH, and the concentration of the organic modifier. The temperature and the nature and strength of the buffer are also known‐to affect the stability of the chiral selector as well as the enantioseparation. Teicoplanin exhibited some features that were not noted with the other glycopeptide antibiotics. For example, it aggregates (forms micelles) in aqueous solutions and this influences its enantioselectivity. Unlike the other studied glycopeptides, teicoplanin precipitates in alcohol‐water mixtures. It also binds less to the capillary wall than vancomycin as evidenced by the faster electroosmotic flow velocity. The micellization of teicoplanin is pH dependent so that the effect of pH on enantiorecognition is more complex for teicoplanin than for other chiral selectors. Also it is shown that the simple model proposed to explain the role of organic modifiers in cyclodextrin‐based CE enantioseparations may not apply to these and other systems. © 1996 Wiley‐Liss, Inc.