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  • Title: Synthesis and TNF-alpha inducing activities of mycoloyl-arabinan motif of mycobacterial cell wall components.
    Author: Ishiwata A, Akao H, Ito Y, Sunagawa M, Kusunose N, Kashiwazaki Y.
    Journal: Bioorg Med Chem; 2006 May 01; 14(9):3049-61. PubMed ID: 16426852.
    Abstract:
    The extract of the cell wall skeleton of Bacillus Calmette-Guérin (BCG-CWS) from Mycobacterium bovis is known to be an activator of innate immunity. Synthesis of pentaarabinofuranoside as part of the arabinan moiety of BCG-CWS was achieved by double alpha-arabinofuranosylation followed by double beta-arabinofuranosylation with orthogonally protected donors. Mycolic esters of the arabinan in the terminal lipo-arabinan motif of BCG-CWS were synthesized through alkylation of unprotected mycolic acid with bis- and tetra-tosylates of pentaarabinofuranoside. A series of compounds were subjected to a tumor necrosis factor alpha (TNF-alpha) secretion-inducing assay, disclosing aspects of the structure-activity relationship which should be useful in finding the site of the activity.
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