Synthesis and antioxidant capacity of 5-selenopyranose derivatives
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Described is a convenient method for the syntheses of sulfur and selenium containing carbohydrate derivatives of L-gulodeoxynojirimycin and the corresponding C-5 epimer D-mannodeoxynojirimycin. The key step in the synthesis of the latter involves epimerisation of the C-5 hydroxyl group by an oxidation followed by stereo-selective reduction to obtain the desired D-sugar derivative. Both derivatives displayed a dose-dependent prevention of the oxidation of methionine residues on human plasma proteins induced by the inflammatory oxidant hypochlorous acid. The seleno-analogues were considerably more active than their thio-equivalents.
|Chemical communications (Cambridge, England)
|Number of pages
|Published - 14 Sep 2011
- Antioxidants, Blood Proteins, Humans, Organometallic Compounds, Oxidants, Oxidation-Reduction, Peroxidase, Selenium, Sulfides