title: Cis-trans isomerization of nitrofuran derivatives by xanthine oxidase.
abstract: Enzymatic cis-trans isomerization of nitrofuran derivatives was 3-(5-Nitro-2-furyl)-2-(2-furyl)-demonstrated with milk xanthine oxidase. acrylamide (AF-2) and 3-(5-nitro-2-furyl)-2-(5-bromo-2-furyl)acrylamide (NFBFA) were mainly converted from the cis to the trans form by this enzyme supplemented with an electron donor. This enzymatic reaction was further characterized with respect to its cofactor requirements. Finally, a new cis-trans isomerization mechanism, which is based on transfer of a single electron by a nitroreductase such as xanthine oxidase to a nitrofuran derivative to give the anion free radical, was proposed.
authors.affiliation: Faculty of Pharmaceutical Sciences, Kyushu University, Fukuoka, Japan.
authors.forename: K
authors.initials: K
authors.lastname: Tatsumi
authors.forename: S
authors.initials: S
authors.lastname: Kitamur
authors.forename: N
authors.initials: N
authors.lastname: Kog
authors.forename: H
authors.initials: H
authors.lastname: Yoshimura
authors.forename: Y
authors.initials: Y
authors.lastname: Kato
mesh_terms: D000388:Air; D000818:Animals; D002417:Cattle; D003067:Coenzymes / Q000378:metabolism / Q000494:pharmacology; D007535:Isomerases / Q000378:metabolism; D007536:Isomerism; D008892:Milk / Q000201:enzymology; D015394:Molecular Structure; D009581:Nitrofurans / Q000737:chemistry* / Q000378:metabolism*; D010084:Oxidation-Reduction / Q000187:drug effects; D010088:Oxidoreductases / Q000378:metabolism; D013876:Thiophenes / Q000378:metabolism; D014969:Xanthine Oxidase / Q000378:metabolism*
chemical_list: D003067:Coenzymes; D009581:Nitrofurans; D013876:Thiophenes; C028976:3-(5-nitro-2-thienyl)-2-(2-furyl)acrylamide; D010088:Oxidoreductases; D014969:Xanthine Oxidase; D007535:Isomerases