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

• Published in: Bioscience, biotechnology, and biochemistry biotechnology, and biochemistry, 2001-11, Vol.65 (11), p.2472-2481
• Main Authors: Shindo, K. (Kirin Brewery Co. Ltd., Takasaki, Gunma (Japan). Research Labs.), Ohnishi, Y, Chun, H.K, Takahashi, H, Hayashi, M, Saito, A, Iguchi, K, Furukawa, K, Harayama, S, Horinouchi, S, Misawa, N
• Format: Article
• Language: English
• Subjects: Actinomycetales - enzymology; Actinomycetales - genetics; arene dioxygenase; AROMATIC COMPOUNDS; BIODEGRADATION; Biological and medical sciences; Biotechnology; Biotransformation; ESCHERICHIA COLI; Escherichia coli - enzymology; Escherichia coli - genetics; Fundamental and applied biological sciences. Psychology; GENES; Genes, Bacterial; Oxidation-Reduction; Oxygenases - genetics; Oxygenases - metabolism; phenanthridine; POLLUTANTS; Polycyclic Aromatic Hydrocarbons - chemistry; Polycyclic Aromatic Hydrocarbons - metabolism; Pseudomonas - enzymology; Pseudomonas - genetics; STREPTOMYCES; Streptomyces - enzymology; Streptomyces - genetics; Streptomyces lividans; Transformation, Bacterial; tricyclic aromatic compounds
• ISSN: 0916-8451; 1347-6947
• DOI: 10.1271/bbb.65.2472

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 sup1H and sup13 C NMR analyses. Several products, e.g., 4-hydroxyfluorene converted from fluorene, and cis-l, 2-dihydroxy-l, 2-dihydrophenanthridine, cis-9, 10-dihydroxy-9, 10-dihydrophenanthridine, and 10-hydroxyphenanthridine, which were converted from phenanthridine, were novel compounds.