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Chemistry of mycolactones, the causative toxins of Buruli ulcer.

ABSTRACT: 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.

SUBMITTER: Kishi Y 

PROVIDER: S-EPMC3084064 | biostudies-literature | 2011 Apr

REPOSITORIES: biostudies-literature

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Chemistry of mycolactones, the causative toxins of Buruli ulcer.

Kishi Yoshito Y  

Proceedings of the National Academy of Sciences of the United States of America 20110307 17

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. ulcera  ...[more]

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