Chiral separations using the macrocyclic antibiotics: a review

• Published in: Journal of Chromatography A Vol. 906; no. 1; pp. 73 - 89
• Main Authors: Ward, Timothy J, Farris III, Alton B
• Format: Book Review Journal Article
• Language: English
• Published: Netherlands Elsevier B.V 12.01.2001
• Subjects: Aminoglycosides; Ansamycins; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - isolation & purification; Antibiotics; Chromatography, High Pressure Liquid - methods; Electrophoresis, Capillary - methods; Glycopeptides; Macrocyclic antibiotics; Polypeptides; Stereoisomerism; Reviews; Polypeptides; Antibiotics; Enantiomer separation; Aminoglycosides; Ansamycins; Macrocyclic antibiotics; Glycopeptides
• ISSN: 0021-9673
• DOI: 10.1016/S0021-9673(00)00941-9

The macrocyclic antibiotics have recently gained popularity as chiral selectors in CE, HPLC and TLC. The macrocyclic antibiotics used for chiral separations include the ansamycins, the glycopeptides, and the polypeptide antibiotic thiostrepton. Although not strictly considered macrocyclic antibiotics, the aminoglycosides are antibiotics that have been used for chiral separations in CE. More chiral analytes have been resolved using the glycopeptides than with the other macrocyclic antibiotics combined. The glycopeptides vancomycin, ristocetin A and teicoplanin have been used extensively as chiral selectors in CE, with ristocetin A appearing to be the most useful chiral selector followed by vancomycin and teicoplanin, respectively. The macrocyclic antibiotics have also been used as chiral bonded phases in HPLC, and HPLC stationary phases based on vancomycin, ristocetin A and teicoplanin have been commercialized. Ristocetin A seems to be the most useful glycopeptide HPLC bonded phase, but its greater expense can be a drawback. The macrocyclic antibiotics have been used with micelles to improve efficiency, provide unique selectivity, and extend the range of separations to neutral solutes. Changing the macrocyclic antibiotic used in CE or HPLC can significantly alter the enantioselectivity of the separations. In fact, the glycopeptide antibiotics are complementary to one another, where if a partial enantioresolution is obtained with one glycopeptide, there is a high probability that a baseline or better separation can be obtained with another.