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Hydroxylation of ionized aromatics including carboxylic acid or amine using recombinant Streptomyces lividans cells expressing modified biphenyl dioxygenase genes |
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| Authors: | Kazutoshi Shindo Ryoko NakamuraIkuko Chinda Yasuo OhnishiSueharu Horinouchi Haruko TakahashiKazuo Iguchi Shigeaki HarayamaKensuke Furukawa Norihiko Misawa |
| Affiliation: | a Department of Food and Nutrition, Japan Women's University, 2-8-1, Mejirodai, Bunkyo-ku, Tokyo 112-8681, Japan b Central Laboratories for Key Technology, Kirin Brewery Co. Ltd, 1-13-5, Fukuura, Kanazawa-ku, Yokohama 236-0004, Japan c Department of Biotechnology, Graduate School of Agriculture and Life Sciences, The University of Tokyo, Bunkyo-ku, Tokyo 113-8657, Japan d Tokyo University of Pharmacy and Life Science, 1432-1, Horinouchi, Hachioji, Tokyo 192-0392, Japan e Marine Biotechnology Institute, 3-75-1, Heita, Kamaishi 026-0001, Japan f Graduate School of Bioresource and Bioenvironmental Sciences, Kyushu University, 6-10-1, Hakozaki, Fukuoka 812-8581, Japan |
| Abstract: | The bphA1(2072)A2A3A4 gene cluster codes for a shuffled biphenyl dioxygenase holoenzyme with broad substrate specificity. These bphA1(2072)A2A3A4 genes were expressed in the actinomycetes Streptomyces lividans using a thiostrepton-inducible promoter PtipA. Biotransformation experiments of various aromatics including carboxylic acid or amine in their molecular structure, such as 1-naphthoic acid, 2-(1-naphthyl)acetic acid, diphenylamine, and 1-benzyl-4-piperidone, were performed using the recombinant S. lividans cells. These ionized aromatics were converted to the corresponding 1,2-dihydrodiol, mono- or tri-hydroxy forms in 48 h. The structure of the converted products was determined by their EI-MS, 1H- and 13C NMR analysis, and several products were found to be novel compounds. |
| Keywords: | biphenyl dioxygenase biotransformation aromatics Streptomyces lividans |
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