Microbial Hydrocarbon Co-oxidation. III. Isolation and Characterization of an α, α′-Dimethyl-cis, cis-Muconic Acid-producing Strain of Nocardia corallina

Beijerinckia B8/36, when grown with succinate in the presence of dibenzothiophene, accumulated (+)-cis-1,2-dihydroxy-1,2-dihydrodibenzothiophene and dibenzothiophene-5-oxide in the culture medium. Each metabolite was isolated in crystalline form and characterized by a variety of chemical techniques. cis-Naphthalene dihydrodiol dehydrogenase, isolated from Pseudomonas putida, oxidized (+)-cis-1,2-dihydroxy-1,2-dihydrodibenzothiophene to a compound that was tentatively identified as 1,2-dihydroxydibenzothiophene. The same product was formed when crude cell extracts of the parent strain of Beijerinckia oxidized (+)-cis-1,2-dihydroxy-1,2-dihydrodibenzothiophene under anaerobic conditions. Further metabolism of 1,2-dihydroxydibenzothiophene by heat-treated cell extracts led to the formation of 4[2-(3-hydroxy)-thionaphthenyl]-2-oxo-3-butenoic acid. The latter compound was metabolized by crude cell extracts to 3-hydroxy-2-formylthionaphthene. Further degradation of this metabolite was not observed.

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“…to remove acid products (11,12). Cells grown under these conditions always yielded active cell extracts.…”

Section: Methodsmentioning

confidence: 99%

Metabolism of dibenzothiophene by a Beijerinckia species

Laborde¹,

Gibson²

1977

Appl Environ Microbiol

145

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“…An analogous sequence is envisaged for m-xylene. Figure 1 shows one of the two pathways proposed by Jamison et al (13) for the oxidation of p-xylene by N. corallina V-49. From the results reported here, it would seem quite probable that the compound represented by X is cis-3,6-dimethyl-3,5-cyclohexadiene-1, 2-diol (cisp-xylene dihydrodiol).…”

Section: Resultsmentioning

confidence: 99%

“…Also, in experiments not reported here, we have demonstrated that 3-methylpyrocatechol dioxygenase, isolated from cells of P. putida that were grown on toluene, shows very little activity with 3,6dimethylpyrocatechol. It is of interest to note that N. corallina V-49 catalyzes ring cleavage between the hydroxyl groups ("ortho" fission) of 3,6-dimethylpyrocatechol to yield a,a'dimethyl-cis, cis-muconic acid (13). Those microorganisms that can utilize dimethylated aromatic hydrocarbons for growth appear to oxidize one of the methyl groups to a carboxyl group before cleavage of the aromatic nucleus (5,6,16).…”

Section: Resultsmentioning

confidence: 99%

“…Under the same cultural conditions, the above Nocardia strains did not oxidize m-xylene. A different strain (V-49) of N. corallina, in addition to oxidizing p-xylene to p-toluic acid and 2, 3-dihydroxy-p-toluic acid, also produced 3,6dimethylpyrocatechol and a,a'-dimethyl-cis, cis-muconic acid (13). The pathway proposed for the formation of the latter two compounds is shown in Fig.…”

mentioning

confidence: 99%

“…Me4Si. Melting points were obtained by use of a 930 on August 1, 2020 by guest http://jb.asm.org/ Proposed pathway for the oxidation of p-xylene to a,a'-dimethylmuconic acid by N. corallirz V-49(13).…”

mentioning

confidence: 99%

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Bacterial Metabolism of para -and meta -Xylene: Oxidation of the Aromatic Ring

1974

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Pseudomonas putida 39/D oxidized p -xylene to cis -3,6-dimethyl-3,5-cyclohexadiene-1,2-diol ( cis-p -xylene dihydrodiol). The latter compound was isolated in crystalline form and its physical properties were determined. The cis configuration of the hydroxyl groups in the oxidation product was inferred from its ability to form an isopropylidene derivative with 2,2-dimethoxypropane. Acid treatment of cis-p -xylene dihydrodiol resulted in the formation of 2,5-dimethylphenol. A partially purified preparation of cis -toluene dihydrodiol dehydrogenase oxidized cis-p -xylene dihydrodiol to 1,2-dihydroxy-3,6-dimethylbenzene (3,6-dimethylpyrocatechol). P. putida 39/D oxidized m -xylene to a compound whose spectral and chromatographic characteristics were consistent with the structure 3,5-dimethyl-3,5-cyclohexadiene-1,2-diol. This product was very unstable, and all attempts to isolate it led to the formation of 2,4-dimethylphenol.

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Aromatic Hydrocarbons—Benzene and Other Alkylbenzenes

Henderson¹

2001

Patty's Toxicology

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Benzene and its alkyl derivatives are monocyclic aromatic compounds (arenes). The compounds are of considerable economic importance as industrial raw materials, solvents, and components of innumerable commercial and consumer products. The aromatics differ vastly in chemical, physical, and biologic characteristics from the aliphatic and alicyclic hydrocarbons. The aromatics are more toxic to humans and other mammals; of prime importance are ( 1 ) the hematopoietic toxicity of benzene resulting in aplastic anemia in humans and other mammalian species, ( 2 ) benzene‐induced leukemia in humans, and ( 3 ) the cerebellar lesions and loss of central nervous system (CNS) integrative functions in “glue sniffers” exposed to high levels of toluene. The simplest single‐ring aromatic hydrocarbon compound is benzene, the nonsubstituted ring system. When one methyl group is attached to the ring, toluene is formed, and with two attached methyl groups, xylene is formed. Xylene occurs in three isomeric forms. The hemimellitines and mesitylenes possess three methyl groups, durene four, and the penta‐ and hexamethylbenzenes, five and six methyl groups, respectively. Other industrially important compounds are ethylbenzene and isopropylbenzene or cumene.

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Microbial Hydrocarbon Co-oxidation. III. Isolation and Characterization of an α, α′-Dimethyl-cis, cis-Muconic Acid-producing Strain of Nocardia corallina

Cited by 23 publications

References 1 publication

Metabolism of dibenzothiophene by a Beijerinckia species

Metabolism of dibenzothiophene by a Beijerinckia species

Bacterial Metabolism of para -and meta -Xylene: Oxidation of the Aromatic Ring

Aromatic Hydrocarbons—Benzene and Other Alkylbenzenes

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