Evaluation of the macrocyclic antibiotic vancomycin as a chiral selector for capillary electrophoresis
- 1 January 1994
- Vol. 6 (6) , 496-509
- https://doi.org/10.1002/chir.530060609
Abstract
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.Keywords
This publication has 9 references indexed in Scilit:
- Use of a Macrocyclic Antibiotic, Rifamycin B, and Indirect Detection for the Resolution of Racemic Amino Alcohols by CEAnalytical Chemistry, 1994
- Use of a Macrocyclic Antibiotic as the Chiral Selector for Enantiomeric Separations by TLCJournal of Liquid Chromatography, 1994
- Macrocyclic Antibiotics as a New Class of Chiral Selectors for Liquid ChromatographyAnalytical Chemistry, 1994
- Enantiomeric separation of fluorescent, 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate, tagged amino acidsJournal of Chromatography A, 1993
- Using affinity capillary electrophoresis to identify the peptide in a peptide library that binds most tightly to vancomycinThe Journal of Organic Chemistry, 1993
- Theoretical aspects of chiral separation in capillary electrophoresis: II. The role of organic solventJournal of Chromatography A, 1992
- Affinity capillary electrophoresis can simultaneously measure binding constants of multiple peptides to vancomycinThe Journal of Organic Chemistry, 1992
- Vancomycin: structure and transformation to CDP-IJournal of the American Chemical Society, 1983
- Physicochemical properties of vancomycin and iodovancomycin and their complexes with diacetyl-l-lysyl-d-alanyl-d-alanineBiochemical Journal, 1971