Formation of a spirodiazaselenurane and its corresponding azaselenonium derivatives from the oxidation of 2,2'-selenobis(benzamide). Structure, properties and glutathione peroxidase activity.
The oxidation of 2,2'-selenobis(benzamide) with N-chlorosuccinimide or hydrogen peroxide afforded the corresponding stable azaselenonium chloride and hydroxide, respectively. Both structures were characterized by spectroscopic and X-ray crystallographic methods. Each contains a covalent N-Se bond, as well as a noncovalent interaction between the selenium atom and the carbonyl oxygen atom of the other amide moiety. The treatment of the azaselenonium chloride with an excess of potassium hydride in DMSO-d(6) afforded the corresponding spirodiazaselenurane species, which proved hydrolytically unstable, but was characterized by NMR spectroscopy. The azaselenonium chloride displayed significant glutathione peroxidase-like catalytic activity in an assay with benzyl thiol and either hydrogen peroxide or tert-butyl hydroperoxide.
Kuzma
Dusan
D
Department of Chemistry, University of Calgary, Calgary, AB, Canada.
Parvez
Masood
M
Back
Thomas George
TG
D001372:Aza Compounds / Q000138:chemical synthesis*; D001549:Benzamides / Q000737:chemistry*; D018360:Crystallography, X-Ray; D005979:Glutathione Peroxidase / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D016566:Organoselenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction
D001372:Aza Compounds; D001549:Benzamides; D016566:Organoselenium Compounds; D005979:Glutathione Peroxidase