| Photochemistry of Mycolactone A/B, the Causative Toxin of Buruli Ulcer. | |
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MedLine Citation:
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PMID: 23121070 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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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 photo-mycolactones. 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 photo-mycolactones was elucidated via (1) structure determination of the four photo-products in the tetraenoate series; (2) their transformation to the photo-products 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 photo-mycolactones exhibit significantly reduced cytotoxicity, compared with mycolac-tone A/B. |
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Authors:
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Yalan Xing; Sudhir M Hande; Yoshito Kishi |
Publication Detail:
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Type: JOURNAL ARTICLE Date: 2012-11-2 |
Journal Detail:
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Title: Journal of the American Chemical Society Volume: - ISSN: 1520-5126 ISO Abbreviation: J. Am. Chem. Soc. Publication Date: 2012 Nov |
Date Detail:
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Created Date: 2012-11-5 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 7503056 Medline TA: J Am Chem Soc Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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