Hauptseite > Publikationsdatenbank > A novel metabolic pathway for degradation of 4-nonylphenol environmental contaminants by Sphingomonas xenophaga Bayram > print

001     47189
005     20200423204225.0
024 7 _ |a pmid:15665329
|2 pmid
024 7 _ |a 10.1074/jbc.M413446200
|2 DOI
024 7 _ |a WOS:000228444800010
|2 WOS
024 7 _ |a 2128/2668
|2 Handle
037 _ _ |a PreJuSER-47189
041 _ _ |a eng
082 _ _ |a 570
084 _ _ |2 WoS
|a Biochemistry & Molecular Biology
100 1 _ |a Gabriel, F.
|b 0
|0 P:(DE-HGF)0
245 _ _ |a A novel metabolic pathway for degradation of 4-nonylphenol environmental contaminants by Sphingomonas xenophaga Bayram
260 _ _ |a Bethesda, Md.
|b Soc.
|c 2005
300 _ _ |a 15526 - 15533
336 7 _ |a Journal Article
|0 PUB:(DE-HGF)16
|2 PUB:(DE-HGF)
336 7 _ |a Output Types/Journal article
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336 7 _ |a Journal Article
|0 0
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336 7 _ |a ARTICLE
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336 7 _ |a JOURNAL_ARTICLE
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336 7 _ |a article
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440 _ 0 |a Journal of Biological Chemistry
|x 0021-9258
|0 3091
|v 280
500 _ _ |a Record converted from VDB: 12.11.2012
520 _ _ |a Several nonylphenol isomers with alpha-quaternary carbon atoms serve as growth substrates for Sphingomonas xenophaga Bayram, whereas isomers containing hydrogen atoms at the alpha-carbon do not. Three metabolites of 4-(1-methyloctyl)-phenol were isolated in mg quantities from cultures of strain Bayram supplemented with the growth substrate isomer 4-(1-ethyl-1,4-dimethyl-pentyl)-phenol. They were unequivocally identified as 4-hydroxy-4-(1-methyl-octyl)-cyclohexa-2,5-dienone, 4-hydroxy-4-(1-methyl-octyl)-cyclohex-2-enone, and 2-(1-methyl-octyl)-benzene-1,4-diol by high pressure liquid chromatography-mass spectrometry and nuclear magnetic resonance spectroscopy. Furthermore, two metabolites originating from 4-n-nonylphenol were identified as 4-hydroxy-4-nonyl-cyclohexa-2,5-dienone and 4-hydroxy-4-nonyl-cyclohex-2-enone by high pressure liquid chromatography-mass spectrometry. We conclude that nonylphenols were initially hydroxylated at the ipso-position forming 4-alkyl-4-hydroxy-cyclohexa-2,5-dienones. Dienones originating from growth substrate nonylphenol isomers underwent a rearrangement that involved a 1,2-C,O shift of the alkyl moiety as a cation to the oxygen atom of the geminal hydroxy group yielding 4-alkoxyphenols, from which the alkyl moieties can be easily detached as alcohols by known mechanisms. Dienones originating from nongrowth substrates did not undergo such a rearrangement because the missing alkyl substituents at the alpha-carbon atom prevented stabilization of the putative alpha-carbocation. Instead they accumulated and subsequently underwent side reactions, such as 1,2-C,C shifts and dihydrogenations. The ipso-hydroxylation and the proposed 1,2-C,O shift constitute key steps in a novel pathway that enables bacteria to detach alpha-branched alkyl moieties of alkylphenols for utilization of the aromatic part as a carbon and energy source.
536 _ _ |a Chemie und Dynamik der Geo-Biosphäre
|c U01
|2 G:(DE-HGF)
|0 G:(DE-Juel1)FUEK257
|x 0
588 _ _ |a Dataset connected to Web of Science, Pubmed
650 _ 2 |2 MeSH
|a Carbon Isotopes
650 _ 2 |2 MeSH
|a Carbon Radioisotopes
650 _ 2 |2 MeSH
|a Environmental Pollutants: metabolism
650 _ 2 |2 MeSH
|a Isomerism
650 _ 2 |2 MeSH
|a Magnetic Resonance Spectroscopy
650 _ 2 |2 MeSH
|a Mass Spectrometry
650 _ 2 |2 MeSH
|a Phenols: metabolism
650 _ 2 |2 MeSH
|a Sphingomonas: metabolism
650 _ 2 |2 MeSH
|a Time Factors
650 _ 7 |0 0
|2 NLM Chemicals
|a Carbon Isotopes
650 _ 7 |0 0
|2 NLM Chemicals
|a Carbon Radioisotopes
650 _ 7 |0 0
|2 NLM Chemicals
|a Environmental Pollutants
650 _ 7 |0 0
|2 NLM Chemicals
|a Phenols
650 _ 7 |0 104-40-5
|2 NLM Chemicals
|a 4-nonylphenol
650 _ 7 |a J
|2 WoSType
700 1 _ |a Heidelberger, A.
|b 1
|0 P:(DE-HGF)0
700 1 _ |a Rentsch, D.
|b 2
|0 P:(DE-HGF)0
700 1 _ |a Giger, W.
|b 3
|0 P:(DE-HGF)0
700 1 _ |a Günther, K.
|b 4
|u FZJ
|0 P:(DE-Juel1)129325
700 1 _ |a Kohler, H.-P.
|b 5
|0 P:(DE-HGF)0
773 _ _ |a 10.1074/jbc.M413446200
|g Vol. 280, p. 15526 - 15533
|p 15526 - 15533
|q 280<15526 - 15533
|0 PERI:(DE-600)1474604-9
|t The @journal of biological chemistry
|v 280
|y 2005
|x 0021-9258
856 7 _ |u http://dx.doi.org/10.1074/jbc.M413446200
|u http://hdl.handle.net/2128/2668
856 4 _ |u https://juser.fz-juelich.de/record/47189/files/74409.pdf
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