The synthesis of methyl 4-(2-octadecylpropen-1-yl)butanoate: a possible inhibitor in mycolic acid biosynthesis

Article abstract of DOI:10.1016/0009-3084(93)90028-2

The high molecular weight 2-alkyl-3-hydroxy mycolic acids are key structural components of the cell envelope of pathogenic mycobacteria such as Mycobacterium tuberculosis.It has been shown recently that (Z)-tetracos-5-enoic acid is a key initial intermediate in mycolic acid biosynthesis in extracs of Mycobacterium smegmatis.This acid is presumably formed by desaturation of tetracosanoate, and previous studies on oleic acid biosynthesis suggest that a cycloproene analogue may be a potential inhibitor.This communication describes the synthesis of methyl 4-(2-octadecylcyclopropen-1-yl)butanoate, which is shown elsewhere to be an inhibitor of the initial stages of mycolic acid synthesis. Key words: Mycobacteria; Mycolic acids; Cyclopropene fatty acid; Biosynthetic inhibitor