Molecular Geometry and Carcinogenic Activity of Aromatic Compounds. New Perspectives

Arcos, Joseph C.; Argus, Mary F.

doi:10.1016/s0065-230x(08)60390-5

Cited by 121 publications

(26 citation statements)

References 282 publications

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“…72) CAR is used as a chemical feedstock for the production of dyes, medicines, and plastics, and is known to possess mutagenic and toxic activities 73) and also to be a recalcitrant molecule. As shown in Table 1, several CAR-using bacteria were isolated by enrichment culture, with CAR as a sole source of carbon and energy, or of carbon, nitrogen, and energy.…”

Section: )mentioning

confidence: 99%

Molecular Bases of Aerobic Bacterial Degradation of Dioxins: Involvement of Angular Dioxygenation

Nojiri

Omori

2002

Bioscience, Biotechnology, and Biochemistry

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Section: )mentioning

confidence: 99%

Molecular Bases of Aerobic Bacterial Degradation of Dioxins: Involvement of Angular Dioxygenation

Nojiri

Omori

2002

Bioscience, Biotechnology, and Biochemistry

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“…While CAR is used as a chemical feedstock for the production of dyes, medicines, and plastics, CAR is known to possess mutagenic and toxic activities (Arcos and Argus, 1968) and also to be a recalcitrant molecule.…”

Section: Microbial Degradation Of Carmentioning

confidence: 99%

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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“…1,2) CAR-degrading bacteria have previously been isolated from the terrestrial environment, including Pseudomonas resinovorans CA10 and Novosphingobium sp. KA1 sp.…”

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confidence: 99%

“…KA1, which are gramnegative, and Nocardioides aromaticivorans IC177, which is gram-positive. 1,[4][5][6][7] The car gene clusters of these strains comprise carAa, carAc, and carAd (however, carAd of strain KA1 has not been identified to date), which encode a CAR 1,9a-dioxygenase (CARDO); carBa and carBb, the small and large subunits of the meta-cleavage enzyme; and carC, the meta-cleavage compound hydrolase. 8,9) The car genes of strains CA10 and KA1 are organized as carAaBaBbCAcAd and carAaBaBbCAc, respectively, while those of strain IC177 are carAaCBaBbAcAd (Fig.…”

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Characterization and genetic analyses of a carbazole-degrading gram-positive marine isolate, Janibacter sp. strain OC11

Oba

Suzuki

Maeda

et al. 2014

Bioscience, Biotechnology, and Biochemistry

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Strain OC11 was isolated from seawater sampled at the coast of Chiba, Japan, in artificial seawater medium with carbazole (CAR) as the sole carbon source. Its 16S ribosomal RNA gene sequence suggested that strain OC11 belongs to the genus Janibacter. The CAR-degradation genes (car genes) of strain OC11 were PCR amplified, using degenerate primers designed based on the car gene sequences of other CAR-degrading bacteria. Complete nucleotide sequences encoding six complete open reading frames were determined, and the first known ferredoxin reductase gene (carAd) was found from a CAR-degrading bacterium isolated from the marine environment. An experiment using a mutant strain suggested that the car genes of strain OC11 are functional in CAR degradation. Southern hybridization indicated that strain OC11 had one car gene cluster in vivo. RT-PCR revealed that transcription of carOC11 constitutes an operon.

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Molecular Geometry and Carcinogenic Activity of Aromatic Compounds. New Perspectives

Cited by 121 publications

References 282 publications

Molecular Bases of Aerobic Bacterial Degradation of Dioxins: Involvement of Angular Dioxygenation

Molecular Bases of Aerobic Bacterial Degradation of Dioxins: Involvement of Angular Dioxygenation

Bacterial degradation of aromatic compounds via angular dioxygenation.

Characterization and genetic analyses of a carbazole-degrading gram-positive marine isolate, Janibacter sp. strain OC11

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