Cis-trans isomerization of the (5-nitro-2-furyl)acrylamide, AF-2, initiated by ascorbate, glutathione, Fe(II) and OH-.
The cis-trans isomerization of the (5-nitro-2-furyl)acrylamide, AF-2, has been investigated using some important biological reducing agents to initiate reaction. Physiological concentrations of L-ascorbic acid, glutathione and iron(II) all accomplish isomerization in a catalytic manner over a period of minutes. Base-catalysed isomerization has also been observed. In all cases, the presence of oxygen severely inhibits isomerization. It is proposed that the mechanism involves a free-radical chain process; AF-2 or analogues are thus extremely sensitive probes for the generation of nitro radicals in biochemical reducing systems because of the high efficiency of isomerization.
D001205:Ascorbic Acid / Q000494:pharmacology*; D005296:Ferrous Compounds / Q000494:pharmacology*; D005668:Furylfuramide / Q000378:metabolism*; D005978:Glutathione / Q000494:pharmacology*; D006878:Hydroxides / Q000494:pharmacology*; D017665:Hydroxyl Radical; D007501:Iron / Q000494:pharmacology*; D007536:Isomerism; D008433:Mathematics; D009581:Nitrofurans / Q000378:metabolism*; D013816:Thermodynamics
D005296:Ferrous Compounds; D006878:Hydroxides; D009581:Nitrofurans; D005668:Furylfuramide; D017665:Hydroxyl Radical; D007501:Iron; D005978:Glutathione; D001205:Ascorbic Acid