Synthesis of 2-deoxy-2-C-alkylglucosides of myo-inositol as possible inhibitors of a N-deacetylase enzyme in the biosynthesis of mycothiol

Bioorganic & Medicinal Chemistry Letters
David W GammonTheophilus T Mudzunga

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.

References

Jul 18, 2001·Journal of the American Chemical Society·H C Hang, C R Bertozzi
Apr 4, 2002·Journal of the American Chemical Society·Gillian M NicholasCarole A Bewley

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Citations

May 7, 2010·Organic Letters·Kehinde AjayiSpencer Knapp
Sep 6, 2008·Microbiology and Molecular Biology Reviews : MMBR·Gerald L NewtonRobert C Fahey
Dec 26, 2013·Bioorganic Chemistry·S S Nilewar, M K Kathiravan
Nov 26, 2008·Natural Product Reports·Vishnu Karthik Jothivasan, Chris J Hamilton
Mar 16, 2016·Beilstein Journal of Organic Chemistry·Shino Manabe, Yukishige Ito
Aug 31, 2006·The Journal of Biological Chemistry·Gerald L NewtonRobert C Fahey
Apr 23, 2021·Organic & Biomolecular Chemistry·Gefei LiShin-Ichiro Shoda

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