Isolation and Characterization of the Genes Encoding a Novel Oxygenase Component of Angular Dioxygenase from the Gram-Positive Dibenzofuran-Degrader Terrabacter sp. Strain DBF63

Kasuga, Kano; Habe, Hiroshi; Chung, Jane; Yoshida, Takako; Nojiri, Hideaki; Yamane, Hisakazu; Omori, Toshio

doi:10.1006/bbrc.2001.4763

Cited by 79 publications

(82 citation statements)

References 40 publications

(34 reference statements)

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“…To our knowledge, six genes encoding angular dioxygenase have been reported Dehmel et al, 1995;Kasuga et al, 2001;Ouchiyama et al, 1998;Sato et al, 1997a;Shepherd and Lloyd-Jones, 1998). The genes encoding CAR-degradation enzymes isolated from P. stutzeri strain OM1 were nearly identical to those from P. resinovorans strain CA10 (Ouchiyama et al, 1998), suggesting that the gene cluster isolated from strain OM1 is a different allele of the CAR-degrading car gene cluster isolated from strain CA10.…”

Section: Genetic and Biochemical Characterization Of Degradation Pathmentioning

confidence: 92%

“…strain HH69 DF 4,4a-dioxygenase DF, DD Fortnagel et al, 1990;Harms et al, 1990Harms et al, , 1991Harms et al, , 1995Schreiner et al, 1997 Sphingomonas wittichii strain RW1 DF 4,4a-dioxygenase DF, DD, 9-Fluorenone Timmis, 1997, 1998;, (Dioxin dioxygenase) 1999, 2000Bertini et al, 1995;Halden et al, 1999;Happe et al, 1993;Keim et al, 1999;Megharaj et al, 1997;Schläfli et al, 1995;Wilkes et al, 1996;Wittich et al, 1992;Yabuuchi et al, 2001 Terrabacter sp. strain DBF63 DF 4,4a-dioxygenase DF, FN Habe et al, 2001;Kasuga et al, 1997Kasuga et al, , 2001Monna et al, 1993 Sphingomonas sp. strain HH19k DF 4,4a-dioxygenase DF Zehnder, 1994, 1995 Sphingomonas sp.…”

Section: Microbial Degradation Of Df Dd and Fnmentioning

confidence: 99%

“…Recently, Kasuga et al (2001) succeeded in cloning the dbfA1 and dbfA2 genes, which encode the large 296 NOJIRI, HABE, and OMORI Vol. 47 Fig.…”

Section: Df/dd/fn Degradation By Terrabacter Sp Strain Dbf63mentioning

confidence: 99%

“…Genetic organization of loci encompassing the genes involved in dibenzofuran (DF) degradation by Terrabacter sp. strain DBF63 (Kasuga et al, 1997(Kasuga et al, , 2001.…”

Section: Df/dd/fn Degradation By Terrabacter Sp Strain Dbf63mentioning

confidence: 99%

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Bacterial degradation of aromatic compounds via angular dioxygenation.

Nojiri

Habe

Omori

2001

J. Gen. Appl. Microbiol.

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Dioxygenation is one of the important initial reactions of the bacterial degradation of various aromatic compounds. Aromatic compounds, such as biphenyl, toluene, and naphthalene, are dioxygenated at lateral positions of the aromatic ring resulting in the formation of cis-dihydrodiol. This "normal" type of dioxygenation is termed lateral dioxygenation. On the other hand, the analysis of the bacterial degradation of fluorene (FN) analogues, such as 9-fluorenone, dibenzofuran (DF), carbazole (CAR), and dibenzothiophene (DBT)-sulfone, and DF-related diaryl ether compounds, dibenzo-p-dioxin (DD) and diphenyl ether (DE), revealed the presence of the novel mode of dioxygenation reaction for aromatic nucleus, generally termed angular dioxygenation. In this atypical dioxygenation, the carbon bonded to the carbonyl group in 9-fluorenone or to heteroatoms in the other compounds, and the adjacent carbon in the aromatic ring are both oxidized. Angular dioxygenation of DF, CAR, DBT-sulfone, DD, and DE produces the chemically unstable hemiacetal-like intermediates, which are spontaneously converted to 2,2,3-trihydroxybiphenyl, 2-aminobiphenyl-2,3-diol, 2,3-dihydroxybiphenyl-2-sulfinate, 2,2,3-trihydroxydiphenyl ether, and phenol and catechol, respectively. Thus, angular dioxygenation for these compounds results in the cleavage of the three-ring structure or DE structure. The angular dioxygenation product of 9-fluorenone, 1-hydro-1,1a-dihydroxy-9-fluorenone is a chemically stable cis-diol, and is enzymatically transformed to 2-carboxy-2,3-dihydroxybiphenyl. 2-Substituted 2,3-dihydroxybiphenyls formed by angular dioxygenation of FN analogues are degraded to monocyclic aromatic compounds by meta cleavage and hydrolysis. Thus, after the novel angular dioxygenation, subsequent degradation pathways are homologous to the corresponding part of that of biphenyl. Compared to the bacterial strains capable of catalyzing lateral dioxygenation, few bacteria having angular dioxygenase have been reported. Only a few degradation pathways, CARdegradation pathway of Pseudomonas resinovorans strain CA10, DF/DD-degradation pathway of Sphingomonas wittichii strain RW1, DF/DD/FN-degradation pathway of Terrabacter sp. strain DBF63, and carboxylated DE-degradation pathway of P. pseudoalcaligenes strain POB310, have been investigated at the gene level. As a result of the phylogenetic analysis and the comparison of substrate specificity of angular dioxygenase, it is suggested that this atypical mode of dioxygenation is one of the oxygenation reactions originating from the relaxed substrate specificity of the Rieske nonheme iron oxygenase superfamily. Genetic characterization of the degradation pathways of these compounds suggests the possibility that the respective genetic elements constituting the entire catabolic pathway have been recruited from various other bacteria and/or other genetic loci, and that these pathways have not evolutionary matured.

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Section: Genetic and Biochemical Characterization Of Degradation Pathmentioning

confidence: 92%

Section: Microbial Degradation Of Df Dd and Fnmentioning

confidence: 99%

“…Recently, Kasuga et al (2001) succeeded in cloning the dbfA1 and dbfA2 genes, which encode the large 296 NOJIRI, HABE, and OMORI Vol. 47 Fig.…”

Section: Df/dd/fn Degradation By Terrabacter Sp Strain Dbf63mentioning

confidence: 99%

“…Genetic organization of loci encompassing the genes involved in dibenzofuran (DF) degradation by Terrabacter sp. strain DBF63 (Kasuga et al, 1997(Kasuga et al, , 2001.…”

Section: Df/dd/fn Degradation By Terrabacter Sp Strain Dbf63mentioning

confidence: 99%

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Bacterial degradation of aromatic compounds via angular dioxygenation.

Nojiri

Habe

Omori

2001

J. Gen. Appl. Microbiol.

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“…When grown on DF, Terrabacter sp. strains DBF63, DPO 360, and DPO1361-the latter a heterotypic synonym to Janibacter terrae-produced intermediates 2,2¢,3-trihydroxybiphenyl and salicylic acid by way of initial dioxygenation by angular dioxygenase [15,16,20,26]. Salicylic acid can be converted to catechol and gentisic acid [16].…”

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confidence: 99%

Biodegradation of Dibenzofuran by Janibacter terrae Strain XJ-1

Jin

Zhu

et al. 2006

Curr Microbiol

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Abstract. The dibenzofuran (DF)-degrading bacterium, Janibacter terrae strain XJ-1, was isolated from sediment from East Lake in Wuhan, China. This strain grows aerobically on DF as the sole source of carbon and energy; it has a doubling time of 12 hours at 30°C; and it almost completely degraded 100 mg/L )1 DF in 5 days, producing 2,2¢,3-trihydroxybiphenyl, salicylic acid, gentisic acid, and other metabolites. The dbdA (DF dioxygenase) gene cluster in the strain is almost identical to that on a large plasmid in Terrabacter sp. YK3. Unlike Janibacter sp. strain YY-1, XJ-1 accumulates gentisic acid rather than catechol as a final product of DF degradation.

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