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INTERNATIONAL JOURNAL OF PHARMACEUTICAL RESEARCH

A Step Towards Excellence
Published by : Advanced Scientific Research
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0975-2366
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IJPR 9[3] July - September 2017 Special Issue

July - September 9[3] 2017

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Synthesis of Trehalose 4’,6’- Diesters and 2,3,2’,3’- tetra esters

Author: RWOA’A HAMEED
Abstract: Glycolipids (trehalose-6,6‘-dimycolates) found associated with the cell walls of mycobacteria as very complex mixtures. Cord factors are very strong signalling agents in the immune system. Synthetic analogues should be useful for diagnosis and treatment of TB, asthma, allergies and other immune system diseases. Trehalose dimycolate (TDM) is a molecule produced by Mycobacterium tuberculosis (Mb) and other mycobacteria. Trehalose monomycolate (TMM) is precursor of TDM, and is involved in providing mycolic acid to the cell wall arabinogalactan in order to form m-AGP complex. In this report, have been describe the synthesis ofregioselective monoacylation, by the protection of the a,a’-D-trehalose in the position of 4,6, 4’,6’ Di-O-benzylidene and 4’,6’-O-benzylidene by changing the equivalents and then are coupled different fatty acids with protected trehalose to get tetraesters and diester. The final step was deprotection trehalose in order to get the final results,have got synthesis six tetraesters and three diester of a,a’-Dtrehalose.. The synthesis of these compounds sets the stage for future biochemical studies to identify mycobacterium tuberculosis.
Keyword: TMM, TDM, Synthesis, Diesters, Tetra esters
DOI: https://doi.org/10.31838/ijpr/2019.11.01.068
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