The conformations of the macrolide antibiotics erythromycin A, azithromycin and clarithromycin in aqueous solution: A 1H NMR study

Abida Awan, Richard J. Brennan, Andrew C. Regan, Jill Barber

    Research output: Contribution to journalArticlepeer-review

    Abstract

    The conformations of the macrolide antibiotics erythromycin A, clarithromycin and azithromycin in aqueous solution have been determined. All three drugs were found to exist predominantly in a "folded-out" conformation with the sugars in the chair-chair up-up form. In the case of clarithromycin this result is in agreement with the published literature; previous reports suggest that the erythromycin A sugars adopt boat conformations and that azithromycin has a significant folded-in contribution. The discrepancies are discussed in full. Erythromycin A 9-ketone was found to be flexible in the C6-C12 region. We present evidence for a new minor conformation (the 8-endo folded-out conformation) intermediate between the folded-out and folded-in conformations. Evidence for traces of other minor conformations s presented for erythromycin and azithromycin, whereas clarithromycin is conformationally very stable.
    Original languageEnglish
    Pages (from-to)1645-1652
    Number of pages7
    JournalJournal of the Chemical Society. Perkin Transactions 2
    Issue number8
    Publication statusPublished - Aug 2000

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