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Photochemistry of mycolactone A/B, the causative toxin of Buruli ulcer
- Source :
- Journal of the American Chemical Society. 134(46)
- Publication Year :
- 2012
-
Abstract
- Photochemistry of mycolactone A/B and related unsaturated fatty acid esters is reported. On exposure to visible light, mycolactone A/B gave a mixture of four photomycolactones. Pentaenoates and tetraenoates, representing the unsaturated fatty acid portion of mycolactone A/B, were found to show the reactivity profile parallel with that of mycolactone A/B. The structure of the four photomycolactones was elucidated via (1) structure determination of the four photoproducts in the tetraenoate series; (2) their transformation to the photoproducts in the pentaenoate and then mycolactone series. Triplet quenchers did not affect the photochemical transformation, thereby indicating an event at the singlet state. A concerted, photochemically allowed [4πs + 2πa] cycloaddition was suggested to account for the observed result. This study provided the structurally defined and homogeneous material, which allowed demonstration that photomycolactones exhibit significantly reduced cytotoxicity, compared with mycolactone A/B.
- Subjects :
- Buruli ulcer
Molecular Structure
Chemistry
Toxin
Stereoisomerism
General Chemistry
medicine.disease
Photochemistry
medicine.disease_cause
Photochemical Processes
Biochemistry
Catalysis
Cycloaddition
chemistry.chemical_compound
Colloid and Surface Chemistry
medicine
Humans
Singlet state
Macrolides
Cytotoxicity
Mycolactone
Buruli Ulcer
Unsaturated fatty acid
Subjects
Details
- ISSN :
- 15205126
- Volume :
- 134
- Issue :
- 46
- Database :
- OpenAIRE
- Journal :
- Journal of the American Chemical Society
- Accession number :
- edsair.doi.dedup.....a45511925925eb075045df4da7bd12d7