THE SYNTHESIS OF METHYL 4-(2-OCTADECYLCYCLOPROPEN-1-YL)BUTANOATE - A POSSIBLE INHIBITOR IN MYCOLIC ACID BIOSYNTHESIS

The high molecular weight 2-alkyl-3-hydroxy mycolic acids are key stru ctural components of the cell envelope of pathogenic mycobacteria such as Mycobacterium tuberculosis. It has been shown recently that (Z)-te tracos-5-enoic acid is a key initial intermediate in mycolic acid bios ynthesis in extracts of Mycobacterium smegmatis. This acid is presumab ly for-med by desaturation of tetracosanoate, and previous studies on oleic acid biosynthesis suggest that a cyclopropene analogue may be a potential inhibitor. This communication describes the synthesis of met hyl 4-(2-octadecylcyclopropen-1-yl)butanoate, which is shown elsewhere to be an inhibitor of the initial stages of mycolic acid synthesis.