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000047189 0247_ $$2DOI$$a10.1074/jbc.M413446200
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000047189 084__ $$2WoS$$aBiochemistry & Molecular Biology
000047189 1001_ $$0P:(DE-HGF)0$$aGabriel, F.$$b0
000047189 245__ $$aA novel metabolic pathway for degradation of 4-nonylphenol environmental contaminants by Sphingomonas xenophaga Bayram
000047189 260__ $$aBethesda, Md.$$bSoc.$$c2005
000047189 300__ $$a15526 - 15533
000047189 3367_ $$0PUB:(DE-HGF)16$$2PUB:(DE-HGF)$$aJournal Article
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000047189 440_0 $$03091$$aJournal of Biological Chemistry$$v280$$x0021-9258
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000047189 520__ $$aSeveral 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.
000047189 536__ $$0G:(DE-Juel1)FUEK257$$2G:(DE-HGF)$$aChemie und Dynamik der Geo-Biosphäre$$cU01$$x0
000047189 588__ $$aDataset connected to Web of Science, Pubmed
000047189 650_2 $$2MeSH$$aCarbon Isotopes
000047189 650_2 $$2MeSH$$aCarbon Radioisotopes
000047189 650_2 $$2MeSH$$aEnvironmental Pollutants: metabolism
000047189 650_2 $$2MeSH$$aIsomerism
000047189 650_2 $$2MeSH$$aMagnetic Resonance Spectroscopy
000047189 650_2 $$2MeSH$$aMass Spectrometry
000047189 650_2 $$2MeSH$$aPhenols: metabolism
000047189 650_2 $$2MeSH$$aSphingomonas: metabolism
000047189 650_2 $$2MeSH$$aTime Factors
000047189 650_7 $$00$$2NLM Chemicals$$aCarbon Isotopes
000047189 650_7 $$00$$2NLM Chemicals$$aCarbon Radioisotopes
000047189 650_7 $$00$$2NLM Chemicals$$aEnvironmental Pollutants
000047189 650_7 $$00$$2NLM Chemicals$$aPhenols
000047189 650_7 $$0104-40-5$$2NLM Chemicals$$a4-nonylphenol
000047189 650_7 $$2WoSType$$aJ
000047189 7001_ $$0P:(DE-HGF)0$$aHeidelberger, A.$$b1
000047189 7001_ $$0P:(DE-HGF)0$$aRentsch, D.$$b2
000047189 7001_ $$0P:(DE-HGF)0$$aGiger, W.$$b3
000047189 7001_ $$0P:(DE-Juel1)129325$$aGünther, K.$$b4$$uFZJ
000047189 7001_ $$0P:(DE-HGF)0$$aKohler, H.-P.$$b5
000047189 773__ $$0PERI:(DE-600)1474604-9$$a10.1074/jbc.M413446200$$gVol. 280, p. 15526 - 15533$$p15526 - 15533$$q280<15526 - 15533$$tThe @journal of biological chemistry$$v280$$x0021-9258$$y2005
000047189 8567_ $$uhttp://hdl.handle.net/2128/2668$$uhttp://dx.doi.org/10.1074/jbc.M413446200
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