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000056261 0247_ $$2pmid$$apmid:17369338
000056261 0247_ $$2pmc$$apmc:PMC1907130
000056261 0247_ $$2DOI$$a10.1128/AEM.02994-06
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000056261 084__ $$2WoS$$aBiotechnology & Applied Microbiology
000056261 084__ $$2WoS$$aMicrobiology
000056261 1001_ $$0P:(DE-HGF)0$$aGabriel, F. L. P.$$b0
000056261 245__ $$aElucidation of the ipso-substitution mechanism for side-chain cleavage of alpha-quaternary 4-nonylphenols and 4-t-butoxyphenol in Sphingobium xenophagum Bayram
000056261 260__ $$aWashington, DC [u.a.]$$bSoc.$$c2007
000056261 300__ $$a3320 - 3326
000056261 3367_ $$0PUB:(DE-HGF)16$$2PUB:(DE-HGF)$$aJournal Article
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000056261 440_0 $$08561$$aApplied and Environmental Microbiology$$v73$$x0099-2240$$y10
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000056261 520__ $$aRecently we showed that degradation of several nonylphenol isomers with alpha-quaternary carbon atoms is initiated by ipso-hydroxylation in Sphingobium xenophagum Bayram (F. L. P. Gabriel, A. Heidlberger, D. Rentsch, W. Giger, K. Guenther, and H.-P. E. Kohler, J. Biol. Chem. 280:15526-15533, 2005). Here, we demonstrate with 18O-labeling experiments that the ipso-hydroxy group was derived from molecular oxygen and that, in the major pathway for cleavage of the alkyl moiety, the resulting nonanol metabolite contained an oxygen atom originating from water and not from the ipso-hydroxy group, as was previously assumed. Our results clearly show that the alkyl cation derived from the alpha-quaternary nonylphenol 4-(1-ethyl-1,4-dimethyl-pentyl)-phenol through ipso-hydroxylation and subsequent dissociation of the 4-alkyl-4-hydroxy-cyclohexadienone intermediate preferentially combines with a molecule of water to yield the corresponding alcohol and hydroquinone. However, the metabolism of certain alpha,alpha-dimethyl-substituted nonylphenols appears to also involve a reaction of the cation with the ipso-hydroxy group to form the corresponding 4-alkoxyphenols. Growth, oxygen uptake, and 18O-labeling experiments clearly indicate that strain Bayram metabolized 4-t-butoxyphenol by ipso-hydroxylation to a hemiketal followed by spontaneous dissociation to the corresponding alcohol and p-quinone. Hydroquinone effected high oxygen uptake in assays with induced resting cells as well as in assays with cell extracts. This further corroborates the role of hydroquinone as the ring cleavage intermediate during degradation of 4-nonylphenols and 4-alkoxyphenols.
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000056261 650_2 $$2MeSH$$aBiodegradation, Environmental
000056261 650_2 $$2MeSH$$aCyclohexanes: metabolism
000056261 650_2 $$2MeSH$$aCyclohexenes
000056261 650_2 $$2MeSH$$aGas Chromatography-Mass Spectrometry
000056261 650_2 $$2MeSH$$aMetabolic Networks and Pathways
000056261 650_2 $$2MeSH$$aMolecular Structure
000056261 650_2 $$2MeSH$$aOxygen: metabolism
000056261 650_2 $$2MeSH$$aOxygen Isotopes: metabolism
000056261 650_2 $$2MeSH$$aPhenols: metabolism
000056261 650_2 $$2MeSH$$aSphingomonas: chemistry
000056261 650_2 $$2MeSH$$aSphingomonas: growth & development
000056261 650_2 $$2MeSH$$aSphingomonas: metabolism
000056261 650_7 $$00$$2NLM Chemicals$$aCyclohexanes
000056261 650_7 $$00$$2NLM Chemicals$$aCyclohexenes
000056261 650_7 $$00$$2NLM Chemicals$$aOxygen Isotopes
000056261 650_7 $$00$$2NLM Chemicals$$aPhenols
000056261 650_7 $$00$$2NLM Chemicals$$acyclohexadienone
000056261 650_7 $$0104-40-5$$2NLM Chemicals$$a4-nonylphenol
000056261 650_7 $$0122-94-1$$2NLM Chemicals$$a4-butoxyphenol
000056261 650_7 $$07782-44-7$$2NLM Chemicals$$aOxygen
000056261 650_7 $$2WoSType$$aJ
000056261 7001_ $$0P:(DE-HGF)0$$aCyris, M.$$b1
000056261 7001_ $$0P:(DE-HGF)0$$aJonkers, N.$$b2
000056261 7001_ $$0P:(DE-HGF)0$$aGiger, W.$$b3
000056261 7001_ $$0P:(DE-Juel1)129325$$aGünther, K.$$b4$$uFZJ
000056261 7001_ $$0P:(DE-HGF)0$$aKohler, H.-P. E.$$b5
000056261 773__ $$0PERI:(DE-600)1478346-0$$a10.1128/AEM.02994-06$$gVol. 73, p. 3320 - 3326$$p3320 - 3326$$q73<3320 - 3326$$tApplied and environmental microbiology$$v73$$x0099-2240$$y2007
000056261 8567_ $$2Pubmed Central$$uhttp://www.ncbi.nlm.nih.gov/pmc/articles/PMC1907130
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