A Covalently Bonded Teicoplanin Chiral Stationary Phase for HPLC Enantioseparations

Abstract

A macrocyclic glycopeptide antibiotic containing a hydrophobic "tail" is covalently attached to silica gel via linkage chains. This material is extensively evaluated as a chiral stationary phase (CSP) for HPLC. The relevant structural features of the teicoplanin molecule which make it an effective chiral selector are discussed. The teicoplanin CSP appears to have excellent enantioselectivity for native amino acids, peptides, α‐hydroxycarboxylic acids, and a variety of neutral analytes including cyclic amides and amines. Enantio‐separations can be achieved in the reversed phase, normal phase, and "polar‐organic" modes. This chiral selector is stable and the integrity of the CSP is excellent in all separation modes. Hence it can be considered a highly effective multimodal column. Optimization of these separations is discussed in terms of both selectivity and efficiency. Results indicate that the surface loading of the chiral selector affects all relevant separation parameters. A hypothesis is proposed to explain the enhanced efficiency obtained when using teicoplanin CSPs with higher surface coverage. It appears that teicoplanin is a widely applicable, highly effective chiral selector for HPLC enantioseparations. © 1995 Wiley‐Liss, Inc. Copyright © 1995 Wiley‐Liss, Inc.

Department(s)

Chemistry

Keywords and Phrases

amino acids; enantiomeric separations; macrocyclic antibiotic; teicoplanin

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 1995

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