title: Synthesis of highly hydroxylated aromatics by evolved biphenyl dioxygenase and subsequent dihydrodiol dehydrogenase.
abstract: The evolved bphA1 (2049) gene, in which nine amino acids from the Pseudomonas pseudoalcaligenes KF707 BphA1 were changed to those from the Burkholderia xenovorans LB400 BphA1 (M247I, H255Q, V258I, G268A, D303E, -313G, S324T, V325I, and T376N), was expressed in Escherichia coli along with the bphA2A3A4 and bphB genes derived from strain KF707. This recombinant E. coli cells converted biphenyl and several heterocyclic aromatic compounds into the highly hydroxylated products such as biphenyl-2,3,2',3'-tetraol (from biphenyl), 2-(2,3-dihydroxyphenyl)benzoxazole-4,5-diol (from 2-phenylbenzoxazole), and 2-(2,5-dihydroxyphenyl)benzoxazole-4,5-diol [from 2-(2-hydroxyphenyl)benzoxazole]. The antioxidative activity of these generated compounds was markedly higher than that of the original substrate used.
authors.affiliation: Department of Food and Nutrition, Japan Women's University, 2-8-1 Mejirodai, Bunkyo-ku, Tokyo, 112-8681, Japan. kshindo@fc.jwu.ac.jp
authors.forename: Kazutoshi
authors.initials: K
authors.lastname: Shindo
authors.forename: Yuko
authors.initials: Y
authors.lastname: Shindo
authors.forename: Tomoko
authors.initials: T
authors.lastname: Hasegawa
authors.forename: Ayako
authors.initials: A
authors.lastname: Osawa
authors.forename: Osamu
authors.initials: O
authors.lastname: Kagami
authors.forename: Kensuke
authors.initials: K
authors.lastname: Furukawa
authors.forename: Norihiko
authors.initials: N
authors.lastname: Misawa
mesh_terms: D000595:Amino Acid Sequence; D000818:Animals; D049308:Dioxygenases / Q000502:physiology*; D019020:Directed Molecular Evolution; D004926:Escherichia coli / Q000201:enzymology / Q000235:genetics; D006841:Hydrocarbons, Aromatic / Q000378:metabolism*; D006900:Hydroxylation; D008969:Molecular Sequence Data; D010088:Oxidoreductases / Q000502:physiology*; D051381:Rats
chemical_list: D006841:Hydrocarbons, Aromatic; D010088:Oxidoreductases; D049308:Dioxygenases; C048338:trans-1,2-dihydrobenzene-1,2-diol dehydrogenase