Synthesis of 2-Deoxy-2-C-Alkylglucosides of myo-Inositol as possible inhibitors of a N-Deacetylase enzyme in the biosynthesis of mycothiol

Two new analogues of 1- -1-O-(2-acetamido-2-deoxy-α- -glucopyranosyl)-myo-inositol, a biosynthetic intermediate in the production of mycothiol in the Mycobacteria have been synthesized. Both the 2-deoxy-2-C-(2′-hydroxypropyl)- -glucoside 5, and the 2-deoxy-2-C-(2′-oxopropyl)- -glucoside 6, are derived from fully benzylated 1- -1-O-(2-C-allyl-2-deoxy)- -glucopyranosyl)-myo-inositol 20, readily assembled via a protected 2-C-allyl-2-deoxyglucosyl fluoride. Both 5 and 6 inhibit the incorporation of [3H]inositol by whole cells of Mycobacterium smegmatis into a number of metabolites which contain inositol.