Analysis of the reduction of nitroxides by flavin mononucleotide |
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Authors: | P.D. Morse E.K. Ruuge Michael J. Petro H.M. Swartz |
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Affiliation: | 1. Department of Chemistry, Illinois State University, Normal, IL, USA;2. University of Illinois College of Medicine and Illinois ESR Research Center, Urbana, IL, U.S.A.;3. U.S.S.R. Cardiology Research Center, Institute of Experimental Cardiology, Moscow, U.S.S.R. |
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Abstract: | This article describes a simle method to prepare hydroxylamines from nitroxides by photo-activated flavin mononucleotide. The half-time of reduction varied from 2 to 38.4 s for a series of nitroxides. For most nitroxides short exposures to light (min) were sufficient to produce significant amounts of hydroxylamine; longer periods of exposure increased the yields of other products. Proxyl (2,2,5-trimethyl-5-alkylpyrrolidine-N-oxy) nitroxides were unsually reactive with a much higher yield of products which could not be reoxidized by ferricyanide to the nitroxides. Optimum conditions for reversible reduction depend on the nitroxide and the amounts of other reducible substances such as oxygen and ferricyanide that may be present. |
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Keywords: | Nitroxide spin label Spin label Reduction Flavin Photoreduction ESR FMN flavin mononucleotide 5N10 5DS (5-doxyl-stearic acid) 12 DS 4-dimethylhexadecylamino-2,2,6,6-tetramethylpiperidine-1-oxyl 4-dimethyldodecylamino-2,2,6,6-tetramethylpiperidine-1-oxyl 4-trimethylamino-2,2,6,6-tetramethylpiperidine-1-oxyl 6-PCA 4-carboxyl-2,2,6,6-tetramethylpiperidine-1-oxyl 6-TA 4-amino-2,2,6,6-tetramethylpiperidine-1-oxyl Tempone 4-oxo-2,2,6,6-tetramethylpiperidine-1-oxyl Tempol 4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl 5-TA 3-amino-2,2,5,5,-tetramethylpyrrolidine-1-oxyl 5-PCA 3-carboxyl-2,2,5,5-tetramethylpyrrolidine-1-oxyl EtPr 2,2′,5-trimethyl-5′-ethylpyrrolidine-1-oxyl PrPr 2,2′,5-trimethyl-5′-propylpyrrolidine-1-oxyl BupR 2,2′,5-trimethyl-5′-butylpyrrolidine-1-oxyl HexPr 2,2′,5-trimethyl-5′-hexylpyrrolidine-1-oxyl |
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