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  • 1
    Electronic Resource
    Electronic Resource
    Metabolism of aromatic hydrocarbons by yeasts (1981)
    Springer
    Archives of microbiology 129 (1981), S. 9-13 
    Details
    ISSN: 1432-072X
    Keywords: Naphthalene ; Biphenyl ; Benzo(a)pyrene ; Biotransformation ; Yeasts ; Candida lipolytica
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract Six yeasts were examined for their ability to metabolize naphthalene, biphenyl and benzo(a)pyrene. All of the organisms tested oxidized these aromatic hydrocarbons. Candida lipolytica oxidized naphthalene to 1-naphthol, 2-naphthol, 4-hydroxy-1-tetralone and trans-1,2-dihydroxy-1,2-dihydronaphthalene. The major metabolite was 1-naphthol. C. lipolytica oxidized biphenyl to produce 2-, 3-, and 4-hydroxybiphenyl, 4,4′-dihydroxybiphenyl and 3-methoxy-4-hydroxybiphenyl. 4-Hydroxybiphenyl was the predominant metabolite formed. C. lipolytica oxidized benzo(a)pyrene to 3-hydroxybenzo(a)pyrene and 9-hydroxybenzo(a)pyrene. Metabolites were isolated and identified by absorption spectrophotometry, mass spectrometry and thin-layer, gasliquid and high-pressure liquid chromatography. Where possible the structures of these metabolites were confirmed by comparison with authenic compounds.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00417170
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  • 2
    Electronic Resource
    Electronic Resource
    Evidence for an arene oxide-NIH shift pathway in the transformation of naphthalene to 1-naphthol by Bacillus cereus (1984)
    Springer
    Archives of microbiology 138 (1984), S. 283-286 
    Details
    ISSN: 1432-072X
    Keywords: Bacillus cereus ; Naphthalene ; Biotransformation ; Arene-Oxide ; 1-Naphthol ; NIH Shift
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract Bacillus cereus ATCC 14579 transformed naphthalene predominately to 1-naphthol. Experiments with [14C]naphthalene showed that over a 24 h period, B. cereus oxidized 5.2% of the added naphthalene. 1-Naphthol accounted for approximately 80% of the total metabolites. B. cereus incubated with naphthalene under the presence of 18O2 led to the isolation of 1-naphthol that contained 94% 18O. The metabolism of [1-2H]-and [2-2H]-naphthalene by B. cereus yielded 1-naphthol which retained 95% and 94% deuterium, respectively, as determined by mass spectral analysis. NMR spectroscopic analysis of the deuterated 1-naphthol formed from [1-2H]-naphthalene indicated an NIH shift mechanism in which 19% of the deuterium migrated from the C-1 to the C-2 position. The 18O2 and NIH shift experiments implicate naphthalene-1,2-oxide as an intermediate in the formation of 1-naphthol from naphthalene by B. cereus.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00410891
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    Paper (German National Licenses)
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  • 3
    Electronic Resource
    Electronic Resource
    Biotransformation and toxicity of aniline and aniline derivatives in cyanobacteria (1981)
    Springer
    Archives of microbiology 130 (1981), S. 272-275 
    Details
    ISSN: 1432-072X
    Keywords: Aniline ; Cyanobacteria ; Biotransformation ; Toxicity ; N-Formylation ; N-Acetylation ; Ring hydroxylation
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract Agmenellum quadruplicatum strain PR-6 and Oscillatoria sp. strain JCM grown photoautotrophically in the presence of aniline metabolized the aromatic amine to formanilide, acetanilide and p-aminophenol. The metabolites were isolated by either thin-layer, gas-liquid or high pressure liquid chromatography and identified by comparison of their chromatographic, ultraviolet absorbance and mass spectral properties with those of authentic compounds. The toxicity of aniline derivatives towards Agmenellum quadruplicatum strain PR-6 indicated that the cyanobacterium was extremely sensitive to o-, m- and p-aminophenols, and phenylhydroxylamine.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00425939
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    Paper (German National Licenses)
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  • 4
    Electronic Resource
    Electronic Resource
    Metabolism and toxicity of 1- and 2-methylnaphthalene and their derivatives in cyanobacteria (1983)
    Springer
    Archives of microbiology 136 (1983), S. 177-183 
    Details
    ISSN: 1432-072X
    Keywords: Biotransformation ; Toxicity ; 1-Methylnaphthalene ; 2-Methylnaphthalene ; 1-Hydroxymethylnaphthalene ; 2-Hydroxymethylnaphthalene ; Cyanobacteria
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract Agmenellum quadruplicatum strain PR-6, Oscillatoria sp. strain JCM and Anabaena sp., strain CA grown photoautotrophically in the presence of either 1- or 2-methylnaphthalene oxidized both compounds at the methyl group to form 1-hydroxymethylnaphthalene and 2-hydroxymethylnaphthalene, respectively. Ring hydroxylated metabolites were not detected. The metabolites were isolated by thin-layer, high performance liquid and gas chromatography and identified by comparison of chromatographic and mass spectral properties with those of authentic compounds. The extent of 1- and 2-methylnaphthalene metabolism to ethyl acetate soluble metabolites ranged from 0.7 to 3.2%. Incubation of Agmenellum quadruplicatum strain PR-6 with 2-methylnaphthalene and molecular oxygen-18 led to the isolation of 2-hydroxymethylnaphthalene that contained oxygen-18. The toxicity of naphthalene, 1- and 2-methylnaphthalene and their derivatives on the growth of Agmenellum quadruplicatum strain PR-6 was investigated using the algal lawn technique. Phenol and quinone derivatives of naphthalene, 1- and 2-methylnaphthalene were most inhibitory. Alkyl side chain hydroxylation products, such as the hydroxymethyl derivatives of 1- and 2-methylnaphthalene were more toxic than the parent methylnaphthalenes. 1- and 2-Naphthoic were not toxic to the cyanobacterium.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00409840
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    Paper (German National Licenses)
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  • 5
    Electronic Resource
    Electronic Resource
    Oxidation of biphenyl by the Cyanobacterium, Oscillatoria sp., strain JCM (1980)
    Springer
    Archives of microbiology 125 (1980), S. 203-207 
    Details
    ISSN: 1432-072X
    Keywords: Biphenyl oxidation ; Cyanobacterium ; Oscillatoria ; 4-hydroxybiphenyl formation
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract The oxidation of biphenyl by Cyanobacterium, Oscillatoria sp., strain JCM was studied. The organism grown photoautotrophically in the presence of biphenyl oxidized biphenyl to form 4-hydroxybiphenyl. The structure of the metabolite was elucidated by ultraviolet and mass spectra and shown to be identical to authentic 4-hydroxybiphenyl. In addition this metabolite had properties indentical to 4-hydroxybiphenyl when analyzed by thin-layer and high-pressure liquid chromatography. Experiments with [14C]-biphenyl showed that over a 24 h period the organism oxidized 2.9% of the added biphenyl to ethyl acetate-soluble products.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00446877
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    Paper (German National Licenses)
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