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Title: Photochemistry of Mycolactone A/B, the Causative Toxin of Buruli Ulcer
Authors: Xing, Yalan
Hande, Sudhir M.
Kishi, Yoshito
Keywords: Chemistry
Issue Date: 2012
Publisher: American Chemical Society
Citation: Y. Xing, S. M. Hande, Y. Kishi. “Photochemistry of Mycolactone A/B, the Causative Toxin of Buruli Ulcer” Journal of the American Chemical Society, 2012, 134, 19234.
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.
Description: Crystallographic Information File (.cif) can be opened with a standard text editor application.
ISSN: 1520-5126
Appears in Collections:Chemistry

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