title: 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.
authors.affiliation: ARC Centre of Excellence for Free Radical Chemistry and Biotechnology, Australia. storkeyc@hri.org.au
authors.forename: Corin
authors.initials: C
authors.lastname: Storkey
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Davies
authors.forename: Jonathan M
authors.initials: JM
authors.lastname: White
authors.forename: Carl H
authors.initials: CH
authors.lastname: Schiesser
mesh_terms: D000975:Antioxidants / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001798:Blood Proteins / Q000378:metabolism; D006801:Humans; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D016877:Oxidants / Q000378:metabolism; D010084:Oxidation-Reduction / Q000187:drug effects; D009195:Peroxidase / Q000378:metabolism; D012643:Selenium / Q000737:chemistry*; D013440:Sulfides / Q000737:chemistry
chemical_list: D000975:Antioxidants; D001798:Blood Proteins; D009942:Organometallic Compounds; D016877:Oxidants; D013440:Sulfides; D009195:Peroxidase; D012643:Selenium