Retention mechanism of high-performance liquid chromatographic enantioseparation on macrocyclic glycopeptide-based chiral stationary phases

Research output: Contribution to journalReview article

90 Citations (Scopus)

Abstract

The development of methods for the separation of enantiomers has attracted great interest in the past 20 years, since it became evident that the potential biological or pharmacological applications are mostly restricted to one of the enantiomers. In the past decade, macrocyclic antibiotics have proved to be an exceptionally useful class of chiral selectors for the separation of enantiomers of biological and pharmacological importance by means of high-performance liquid chromatography (HPLC), thin-layer chromatography and electrophoresis. The glycopeptides avoparcin, teicoplanin, ristocetin A and vancomycin have been extensively used as chiral selectors in the form of chiral bonded phases in HPLC, and HPLC stationary phases based on these glycopeptides have been commercialized. In fact, the macrocyclic glycopeptides are to some extent complementary to one another: where partial enantioresolution is obtained with one glycopeptide, there is a high probability that baseline or better separation can be obtained with another. This review sets out to characterize the physicochemical properties of these macrocyclic glycopeptide antibiotics and, through their application, endeavors to demonstrate the mechanism of separation on macrocyclic glycopeptides. The sequence of elution of the stereoisomers and the relation to the absolute configuration are also discussed.

Original languageEnglish
Pages (from-to)1845-1860
Number of pages16
JournalJournal of Chromatography A
Volume1216
Issue number10
DOIs
Publication statusPublished - Mar 6 2009

Keywords

  • Enantiomer separation
  • Glycopeptides
  • HPLC
  • Macrocyclic antibiotics
  • Review

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Retention mechanism of high-performance liquid chromatographic enantioseparation on macrocyclic glycopeptide-based chiral stationary phases'. Together they form a unique fingerprint.

  • Cite this