Chemistry of mycolactones, the causative toxins of Buruli ulcer

Buruli ulcer is a severe and devastating skin disease caused by Mycobacterium ulcerans infection, yet it is one of the most neglected diseases. The causative toxin, referred to as mycolactone A/B, was isolated and characterized as a polyketide-derived macrolide in 1999. The current status of the myc...

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Veröffentlicht in:Proceedings of the National Academy of Sciences - PNAS 2011-04, Vol.108 (17), p.6703-6708
Hauptverfasser: Kishi, Yoshito, Schreiber, Stuart L.
Format: Artikel
Sprache:eng
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Zusammenfassung:Buruli ulcer is a severe and devastating skin disease caused by Mycobacterium ulcerans infection, yet it is one of the most neglected diseases. The causative toxin, referred to as mycolactone A/B, was isolated and characterized as a polyketide-derived macrolide in 1999. The current status of the mycolactone chemistry is described, highlighting the stereochemistry assignment of mycolactone A/B; total synthesis; the structure determination of mycolactone congeners from the human pathogen M. ulcerans, the frog pathogen Mycobacterium liflandii, and the fish pathogen Mycobacterium marinum; the structural diversity in the mycolactone class of natural products; the highly sensitive detection/structure-analysis of mycolactones; and some biological activity.
ISSN:0027-8424
1091-6490
DOI:10.1073/pnas.1015252108