Applied Microbiology and Biotechnology

, Volume 75, Issue 5, pp 1063–1069 | Cite as

Synthesis of highly hydroxylated aromatics by evolved biphenyl dioxygenase and subsequent dihydrodiol dehydrogenase

  • Kazutoshi ShindoEmail author
  • Yuko Shindo
  • Tomoko Hasegawa
  • Ayako Osawa
  • Osamu Kagami
  • Kensuke Furukawa
  • Norihiko Misawa
Biotechnologically Relevant Enzymes and Proteins


The evolved bphA1 (2049) gene, in which nine amino acids from the Pseudomonas pseudoalcaligenes KF707 BphA1 were changed to those from the Burkholderiaxenovorans 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.


Hydroxylated aromatics Biphenyl dioxygenase Dihydrodiol dehydrogenase 



This work was supported in part by the Biotechnology and Medical Technology Development Department of the New Energy and Industrial Technology Development Organization (NEDO).


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Copyright information

© Springer-Verlag 2007

Authors and Affiliations

  • Kazutoshi Shindo
    • 1
    Email author
  • Yuko Shindo
    • 1
  • Tomoko Hasegawa
    • 1
  • Ayako Osawa
    • 1
  • Osamu Kagami
    • 3
  • Kensuke Furukawa
    • 2
  • Norihiko Misawa
    • 3
  1. 1.Department of Food and NutritionJapan Women’s UniversityBunkyo-kuJapan
  2. 2.Graduated School of Bioresource and Bioenvironmental SciencesKyushu UniversityHakozakiJapan
  3. 3.Marine Biotechnology InstituteKamaishi-shiJapan

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