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Chirality

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Chirality is a term that describes the lack of mirror symmetry in an object. In other words, chiral objects cannot be superposed on their mirror images. For example, our feet are chiral, as the mirror image of the left foot, the right foot, cannot be superposed on the left foot.
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Visualization of Bacterial Resistance using Fluorescent Antibiotic Probes

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Chiral separations using the macrocyclic antibiotics: a review.

T J Ward¹, A B Farris

¹Department of Chemistry, Millsaps College, Jackson, MS 39210, USA. wardtj@millsaps.edu

Journal of Chromatography. A

|February 24, 2001

Summary

This summary is machine-generated.

Macrocyclic antibiotics, particularly glycopeptides like vancomycin, are effective chiral selectors in capillary electrophoresis (CE) and HPLC. Different glycopeptides offer complementary selectivity for challenging chiral separations.

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Area of Science:

Analytical Chemistry
Separation Science

Background:

Macrocyclic antibiotics are increasingly utilized as chiral selectors in various chromatographic and electrophoretic techniques.
Glycopeptides, such as vancomycin, ristocetin A, and teicoplanin, have shown significant promise in resolving chiral analytes.

Purpose of the Study:

To review the application of macrocyclic antibiotics as chiral selectors in capillary electrophoresis (CE), high-performance liquid chromatography (HPLC), and thin-layer chromatography (TLC).
To highlight the effectiveness of glycopeptides in chiral separations and compare their utility with other macrocyclic antibiotics.

Main Methods:

Review of literature on the use of macrocyclic antibiotics as chiral selectors in CE and HPLC.
Analysis of enantioselectivity and separation efficiency achieved with different macrocyclic antibiotics, particularly glycopeptides.

Main Results:

Glycopeptides have resolved more chiral analytes than other macrocyclic antibiotics combined.
Ristocetin A, vancomycin, and teicoplanin are effective chiral selectors in CE, with ristocetin A being the most useful.
Commercialized HPLC stationary phases are available based on vancomycin, ristocetin A, and teicoplanin, with ristocetin A showing high utility despite its cost.
Macrocyclic antibiotics, used with micelles, enhance separation efficiency and selectivity for neutral solutes.

Conclusions:

Macrocyclic antibiotics, especially glycopeptides, are versatile and powerful tools for chiral separations in CE and HPLC.
The complementary selectivity of different glycopeptides allows for optimization of challenging enantioseparations.