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-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.
Gammon
David W
DW
Department of Chemistry, University of Cape Town, 7701, Rondebosch, South Africa
Hunter
Roger
R
Steenkamp
Daniel J
DJ
Mudzunga
Theophilus T
TT
D000581:Amidohydrolases / Q000037:antagonists & inhibitors* / Q000378:metabolism; D003545:Cysteine; D004187:Disaccharides / Q000096:biosynthesis*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006020:Glycopeptides; D007294:Inositol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism / Q000494:pharmacology*; D020102:Mycobacterium smegmatis / Q000187:drug effects / Q000254:growth & development; D011720:Pyrazoles; D013438:Sulfhydryl Compounds; D014316:Tritium
D004187:Disaccharides; D004791:Enzyme Inhibitors; D005960:Glucosides; D006020:Glycopeptides; D011720:Pyrazoles; D013438:Sulfhydryl Compounds; C089265:mycothiol; D014316:Tritium; D007294:Inositol; D000581:Amidohydrolases; D003545:Cysteine