Oxygenation reactions of various tricyclic fused aromatic compounds using Escherichia coli and Streptomyces lividans transformants carrying several arene dioxygenase genes.

Article abstract of DOI:10.1271/bbb.65.2472

Bioconversion (biotransformation) experiments on arenes (aromatic compounds), including various tricyclic fused aromatic compounds such as fluorene, dibenzofuran, dibenzothiophene, carbazole, acridene, and phenanthridine, were done using the cells of Escherichia coli transformants expressing several arene dioxygenase genes. E. coli carrying the phenanthrene dioxygenase (phdABCD) genes derived from the marine bacterium Nocardioides sp. strain KP7 converted all of these tricyclic aromatic compounds, while E. coli carrying the Pseudomonas putida F1 toluene dioxygenase (todC1C2BA) genes or the P. pseudoalcaligenes KF707 biphenyl dioxygenase (bphA1A2A3A4) genes was not able to convert these substrates. Surprisingly, E. coli carrying hybrid dioxygenase (todC1::bphA2A3A4) genes with a subunit substitution between the toluene and biphenyl dioxygenases was able to convert fluorene, dibenzofuran, and dibenzothiophene. The cells of a Streptomyces lividans transformant carrying the phenanthrene dioxygenase genes were also evaluated for bioconversion of various tricyclic fused aromatic compounds. The ability of this actinomycete in their conversion was similar to that of E. coli carrying the corresponding genes. Products converted from the aromatic compounds with these recombinant bacterial cells were purified by column chromatography on silica gel, and identified by their MS and 1H and 13C NMR analyses. Several products, e.g., 4-hydroxyfluorene converted from fluorene, and cis-1,2-dihydroxy-1,2-dihydrophenanthridine, cis-9,10-dihydroxy-9,10-dihydrophenanthridine, and 10-hydroxyphenanthridine, which were converted from phenanthridine, were novel compounds.

Full text of DOI:10.1271/bbb.65.2472

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Oxygenation Reactions of Various Tricyclic Fused
Aromatic Compounds Using Escherichia coli and
Streptomyces lividans Transformants Carrying
Several Arene Dioxygenase Genes
Kazutoshi SHINDOa, Yasuo OHNISHIb, Hyo-Kon CHUNb, Haruko TAKAHASHIc, Miki HAYASHId,
Atsushi SAITOe, Kazuo IGUCHIc, Kensuke FURUKAWAf, Shigeaki HARAYAMAe, Sueharu
HORINOUCHIb & Norihiko MISAWAd
a Pharmaceutical Research Laboratories, Kirin Brewery Co., Ltd.
b Department of Biotechnology, Graduate School of Agriculture and Life Sciences, The
University of Tokyo
c Tokyo University of Pharmacy and Life Science
d Central Laboratories for Key Technology, Kirin Brewery Co. Ltd.
e Marine Biotechnology Institute
f Division of Bioresource and Bioenvironmental Sciences, Kyushu University
Published online: 22 May 2014.
To cite this article: Kazutoshi SHINDO, Yasuo OHNISHI, Hyo-Kon CHUN, Haruko TAKAHASHI, Miki HAYASHI, Atsushi SAITO,
Kazuo IGUCHI, Kensuke FURUKAWA, Shigeaki HARAYAMA, Sueharu HORINOUCHI & Norihiko MISAWA (2001) Oxygenation
Reactions of Various Tricyclic Fused Aromatic Compounds Using Escherichia coli and Streptomyces lividans Transformants
Carrying Several Arene Dioxygenase Genes, Bioscience, Biotechnology, and Biochemistry, 65:11, 2472-2481, DOI: 10.1271/
bbb.65.2472
To link to this article: http://dx.doi.org/10.1271/bbb.65.2472
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