Shishmarev, Dmitry; Quiquempoix, Lucas; Fontenelle, Clement Q.; Linclau, Bruno; Kuchel, Philip W. published the artcile< Anomerization of Fluorinated Sugars by Mutarotase Studied Using 19F NMR Two-Dimensional Exchange Spectroscopy>, Reference of 492-62-6, the main research area is anomerization fluorinated monosaccharide mutarotase glucose enzyme mol structure NMR.
Five 19F-substituted glucose analogs were used to probe the activity and mechanism of the enzyme mutarotase by using magnetization-exchange NMR spectroscopy. The sugars (2-fluoro-2-deoxy-d-glucose, FDG2; 3-fluoro-3-deoxy-d-glucose, FDG3; 4-fluoro-4-deoxy-d-glucose, FDG4; 2,3-difluoro-2,3-dideoxy-d-glucose, FDG23; and 2,2,3,3-tetrafluoro-2,3-dideoxy-d-glucose (2,3-dideoxy-2,2,3,3-tetrafluoro-d-erythro-hexopyranose), FDG2233) showed sep. 19F NMR spectroscopic resonances from their resp. α- and β-anomers, thus allowing two-dimensional exchange spectroscopy measurements of the anomeric interconversion at equilibrium, on the time scale of a few seconds. Mutarotase catalyzed the rapid exchange between the anomers of FDG4, but not the other four sugars. This finding, combined with previous work identifying the mechanism of the anomerization by mutarotase, suggests that the rotation around the C1-C2 bond of the pyranose ring is the rate-limiting reaction step. In addition to D-glucose itself, it was shown that all other fluorinated sugars inhibited the FDG4 anomerization, with the tetra-fluorinated FDG2233 being the most potent inhibitor. Inhibition of mutarotase by F-sugars paves the way for the development of novel fluorinated compounds that are able to affect the activity of this enzyme in vitro and in vivo.
Australian Journal of Chemistry published new progress about Anomerization. 492-62-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C6H12O6, Reference of 492-62-6.
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