Synthesis and antioxidant capacity of 5-selenopyranose derivatives

Abstract

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. © The Royal Society of Chemistry 2011.