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@ARTICLE{Gabriel:47189,
      author       = {Gabriel, F. and Heidelberger, A. and Rentsch, D. and Giger,
                      W. and Günther, K. and Kohler, H.-P.},
      title        = {{A} novel metabolic pathway for degradation of
                      4-nonylphenol environmental contaminants by {S}phingomonas
                      xenophaga {B}ayram},
      journal      = {The journal of biological chemistry},
      volume       = {280},
      issn         = {0021-9258},
      address      = {Bethesda, Md.},
      publisher    = {Soc.},
      reportid     = {PreJuSER-47189},
      pages        = {15526 - 15533},
      year         = {2005},
      note         = {Record converted from VDB: 12.11.2012},
      abstract     = {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.},
      keywords     = {Carbon Isotopes / Carbon Radioisotopes / Environmental
                      Pollutants: metabolism / Isomerism / Magnetic Resonance
                      Spectroscopy / Mass Spectrometry / Phenols: metabolism /
                      Sphingomonas: metabolism / Time Factors / Carbon Isotopes
                      (NLM Chemicals) / Carbon Radioisotopes (NLM Chemicals) /
                      Environmental Pollutants (NLM Chemicals) / Phenols (NLM
                      Chemicals) / 4-nonylphenol (NLM Chemicals) / J (WoSType)},
      cin          = {ICG-III},
      ddc          = {570},
      cid          = {I:(DE-Juel1)VDB49},
      pnm          = {Chemie und Dynamik der Geo-Biosphäre},
      pid          = {G:(DE-Juel1)FUEK257},
      shelfmark    = {Biochemistry $\&$ Molecular Biology},
      typ          = {PUB:(DE-HGF)16},
      pubmed       = {pmid:15665329},
      UT           = {WOS:000228444800010},
      doi          = {10.1074/jbc.M413446200},
      url          = {https://juser.fz-juelich.de/record/47189},
}