Premium
Evaluation of the macrocyclic antibiotic vancomycin as a chiral selector for capillary electrophoresis
Author(s) -
Armstrong Daniel W.,
Rundlett Kimber L.,
Chen JingRan
Publication year - 1994
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/chir.530060609
Subject(s) - chemistry , stereocenter , capillary electrophoresis , enantioselective synthesis , vancomycin , glycopeptide , antibiotics , combinatorial chemistry , amide , hydrogen bond , stereochemistry , chromatography , organic chemistry , bacteria , molecule , biochemistry , catalysis , staphylococcus aureus , biology , genetics
Vancomycin is one of a family of related macrocyclic glycopeptide antibiotics that were discovered by scientists at the Eli Lilly Company in the 1950s. It has been used to treat severe staphylococcal infections, particularly when bacterial resistance to other antibiotics has developed. Vancomycin is a naturally occurring chiral compound and has a number of stereogenic centers. Furthermore, it contains a variety of functionalities that are known to be useful for enantioselective interactions (e.g., hydrogen bonding groups, hydrophobic pockets, aromatic groups, amide linkages, etc.). The physicochemical properties of vancomycin, including its stability in solution, are discussed as they pertain to capillary electrophoresis. Over 100 racemates were resolved including many nonsteroidal antiinflammatory drugs, antineoplastic compounds and N ‐derivatized amino acids. Many of these compounds had very high resolution factors. Optimization and the effect of different experimental parameters on the enantioselective separations are discussed. © 1994 Wiley‐Liss, Inc.