Document Detail


Photochemistry of Mycolactone A/B, the Causative Toxin of Buruli Ulcer.
MedLine Citation:
PMID:  23121070     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
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.
Authors:
Yalan Xing; Sudhir M Hande; Yoshito Kishi
Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-11-2
Journal Detail:
Title:  Journal of the American Chemical Society     Volume:  -     ISSN:  1520-5126     ISO Abbreviation:  J. Am. Chem. Soc.     Publication Date:  2012 Nov 
Date Detail:
Created Date:  2012-11-5     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  7503056     Medline TA:  J Am Chem Soc     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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