Evaluation of the Macrocyclic Antibiotic Vancomycin as a Chiral Selector for Capillary Electrophoresis

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. © 1994 Wiley‐Liss, Inc. Copyright © 1994 Wiley‐Liss, Inc.

Department(s)

Chemistry

Comments

National Institute of General Medical Sciences, Grant R01GM036292

Keywords and Phrases

enantiomeric separations; macrocyclic antibiotics capillary electrophoresis; vancomycin

International Standard Serial Number (ISSN)

1520-636X; 0899-0042

Document Type

Article - Journal

Document Version

Citation

File Type

text

Language(s)

English

Rights

© 2024 Wiley, All rights reserved.

Publication Date

01 Jan 1994

PubMed ID

7946976

Link to Full Text

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