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@ARTICLE{Gabriel:47188,
      author       = {Gabriel, F. and Giger, W. and Günther, K. and Kohler,
                      H.-P.},
      title        = {{D}ifferential degradation of nonylphenol isomers by
                      {S}phingomonas xenophaga {B}ayram},
      journal      = {Applied and environmental microbiology},
      volume       = {71},
      issn         = {0099-2240},
      address      = {Washington, DC [u.a.]},
      publisher    = {Soc.},
      reportid     = {PreJuSER-47188},
      pages        = {1123 - 1129},
      year         = {2005},
      note         = {Record converted from VDB: 12.11.2012},
      abstract     = {Sphingomonas xenophaga Bayram, isolated from the activated
                      sludge of a municipal wastewater treatment plant, was able
                      to utilize 4-(1-ethyl-1,4-dimethylpentyl)phenol, one of the
                      main isomers of technical nonylphenol mixtures, as a sole
                      carbon and energy source. The isolate degraded 1 mg of
                      4-(1-ethyl-1,4-dimethylpentyl)phenol/ml in minimal medium
                      within 1 week. Growth experiments with five nonylphenol
                      isomers showed that the three isomers with quaternary
                      benzylic carbon atoms [(1,1,2,4-tetramethylpentyl)phenol,
                      4-(1-ethyl-1,4-dimethylpentyl)phenol, and
                      4-(1,1-dimethylheptyl)phenol] served as growth substrates,
                      whereas the isomers containing one or two hydrogen atoms in
                      the benzylic position [4-(1-methyloctyl)phenol and
                      4-n-nonylphenol] did not. However, when the isomers were
                      incubated as a mixture, all were degraded to a certain
                      degree. Differential degradation was clearly evident, as
                      isomers with more highly branched alkyl side chains were
                      degraded much faster than the others. Furthermore, the C9
                      alcohols 2,3,5-trimethylhexan-2-ol, 3,6-dimethylheptan-3-ol,
                      and 2-methyloctan-2-ol, derived from the three nonylphenol
                      isomers with quaternary benzylic carbon atoms, were detected
                      in the culture fluid by gas chromatography-mass
                      spectrometry, but no analogous metabolites could be found
                      originating from 4-(1-methyloctyl)phenol and
                      4-n-nonylphenol. We propose that 4-(1-methyloctyl)phenol and
                      4-n-nonylphenol were cometabolically transformed in the
                      growth experiments with the mixture but that, unlike the
                      other isomers, they did not participate in the reactions
                      leading to the detachment of the alkyl moiety. This
                      hypothesis was corroborated by the observed accumulation in
                      the culture fluid of an as yet unidentified metabolite
                      derived from 4-(1-methyloctyl)phenol.},
      keywords     = {Alcohols: chemistry / Alcohols: metabolism /
                      Biodegradation, Environmental / Gas Chromatography-Mass
                      Spectrometry / Isomerism / Molecular Structure / Phenols:
                      chemistry / Phenols: metabolism / Sewage: microbiology /
                      Sphingomonas: isolation $\&$ purification / Sphingomonas:
                      metabolism / Alcohols (NLM Chemicals) / Phenols (NLM
                      Chemicals) / Sewage (NLM Chemicals) / 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    = {Biotechnology $\&$ Applied Microbiology / Microbiology},
      typ          = {PUB:(DE-HGF)16},
      pubmed       = {pmid:15746308},
      pmc          = {pmc:PMC1065174},
      UT           = {WOS:000227702900001},
      doi          = {10.1128/AEM.71.3.1123-1129.2005},
      url          = {https://juser.fz-juelich.de/record/47188},
}