Free-radical chain oxidation of 2-nitropropane initiated and propagated by superoxide.
The superoxide radical O2.-, whether produced by the xanthine/xanthine oxidase reaction or infused as KO2, solubilized by a crown ether in dry dimethyl sulphoxide, initiated a free-radical chain oxidation of anionic 2-nitropropane. Superoxide dismutase, but not catalase, inhibited oxidation of the nitroalkane. Xanthine oxidase suffered a syncatalytic inactivation, during the co-oxidation of 2-nitropropane, which was reversed by dialysis. Cyanide exacerbated this syncatalytic inactivation and rendered it irreversible. The frequently observed oxidations of nitroalkanes by flavoenzymes now need to be re-examined to clarify the extent to which O2.--initiated free-radical chain oxidation contributed to the overall nitroalkane oxidation.
D000473:Alkanes / Q000378:metabolism*; D002374:Catalase / Q000378:metabolism; D003486:Cyanides / Q000494:pharmacology; D005609:Free Radicals; D009595:Nitroparaffins / Q000378:metabolism*; D010084:Oxidation-Reduction / Q000187:drug effects; D011407:Propane / Q000031:analogs & derivatives* / Q000378:metabolism; D013481:Superoxides / Q000378:metabolism* / Q000494:pharmacology; D014969:Xanthine Oxidase / Q000037:antagonists & inhibitors / Q000378:metabolism
D000473:Alkanes; D003486:Cyanides; D005609:Free Radicals; D009595:Nitroparaffins; D013481:Superoxides; C039316:potassium superoxide; D002374:Catalase; D014969:Xanthine Oxidase; C016617:2-nitropropane; D011407:Propane