Synthesis and antioxidant capacity of 5-selenopyranose derivatives

Research output: Contribution to journalJournal articleResearchpeer-review

Corin Storkey, Michael Jonathan Davies, Jonathan M White, Carl H Schiesser

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.

Original languageEnglish
JournalChemical communications (Cambridge, England)
Volume47
Issue number34
Pages (from-to)9693-5
Number of pages3
ISSN1359-7345
DOIs
Publication statusPublished - 14 Sep 2011
Externally publishedYes

    Research areas

  • Antioxidants, Blood Proteins, Humans, Organometallic Compounds, Oxidants, Oxidation-Reduction, Peroxidase, Selenium, Sulfides

ID: 129669663