Awesome Chemistry Experiments For 4-Methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside

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In heterogeneous catalysis, catalysts provide a surface to which reactants bind in a process of adsorption. Enzyme inhibitors cause a decrease in the reaction rate of an enzyme-catalyzed reaction. 28244-94-2, Name is 4-Methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside, molecular formula is C21H26O9S. In a Article,once mentioned of 28244-94-2, Synthetic Route of 28244-94-2

(Chemical Equation Presented). Long treatment times, poor drug compliance, and natural selection during treatment of Mycobacterium tuberculosis (Mtb) have given rise to extensively drug-resistant tuberculosis (XDR-TB). As a result, there is a need to identify new antituberculosis drug targets. Mtb GlgE is a maltosyl transferase involved in alpha-glucan biosynthesis. Mutation of GlgE in Mtb increases the concentration of maltose-1-phosphate (M1P), one substrate for GlgE, causing rapid cell death. We have designed 2,5-dideoxy-3-O-alpha-D-glucopyranosyl-2,5-imino-D-mannitol (9) to act as an inhibitor of GlgE. Compound 9 was synthesized using a convergent synthesis by coupling thioglycosyl donor 14 and 5-azido-3-O-benzyl-5-deoxy-1,2-O-isopropylidene-alpha-D-fructopyranose (23) to form disaccharide 24. A reduction and intramolecular reductive amination transformed the intermediate disaccharide 24 to the desired pyrolidine 9. Compound 9 inhibited both Mtb GlgE and a variant of Streptomyces coelicolor (Sco) GlgEI with Ki = 237 ± 27 muM and Ki = 102 ± 7.52 muM, respectively. The results confirm that a Sco GlgE-V279S variant can be used as a model for Mtb GlgE. In conclusion, we designed a lead transition state inhibitor of GlgE, which will be instrumental in further elucidation of the enzymatic mechanism of Mtb GlgE.

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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics