Synthesis of 2-deoxy-2-C-alkylglucosides of myo-inositol as possible inhibitors of a N-deacetylase enzyme in the biosynthesis of mycothiol |
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Authors: | Gammon David W Hunter Roger Steenkamp Daniel J Mudzunga Theophilus T |
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Institution: | Department of Chemistry, University of Cape Town, 7701, Rondebosch, South Africa |
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Abstract: | Two new analogues of 1-D-1-O-(2-acetamido-2-deoxy-alpha-D-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)-D-glucoside 5, and the 2-deoxy-2-C-(2'-oxopropyl)-D-glucoside 6, are derived from fully benzylated 1-D-1-O-(2-C-allyl-2-deoxy)-D-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. |
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