Contribution to the Detection and Identification of Oxidation Metabolites of Nonylphenol in Sphingomonas sp. strain TTNP3
Sphingomonas sp. strain TTNP3 has been previously described as a bacterium that is capable of degrading the technical mixture of nonylphenol (NP) isomers and also the 4(3',5'-dimethyl-3'-heptyl)-phenol single isomer of NP. Until recently, 3,5-dimethyl-3-heptanol was the only reported...
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| Veröffentlicht in: | Biodegradation (Dordrecht) 2007-04, Vol.18 (2), p.233-245 |
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| creator | Corvini, P. F. X Meesters, R Mundt, M Schäffer, A Schmidt, B Schröder, H. -Fr Verstraete, W Vinken, R Hollender, J |
| description | Sphingomonas sp. strain TTNP3 has been previously described as a bacterium that is capable of degrading the technical mixture of nonylphenol (NP) isomers and also the 4(3',5'-dimethyl-3'-heptyl)-phenol single isomer of NP. Until recently, 3,5-dimethyl-3-heptanol was the only reported metabolite of 4(3',5'-dimethyl-3'-heptyl)-phenol. A short time ago, the detection of an intracellular metabolite resulting from the oxidation of 4(3',5'-dimethyl-3'-heptyl)-phenol which was identified as 2(3,5-dimethyl-3-heptyl)-benzenediol has been reported. A decisive element for this identification was the occurrence of some slight differences with the two most probable metabolites i.e. 4(3',5'-dimethyl-3'-heptyl)-resorcinol and 4(3',5'-dimethyl-3'-heptyl)-catechol. These facts led us to hypothesise some NIH shift mechanisms explaining the formation of 2(3',5'-dimethyl-3'-heptyl)-benzenediol. In the present work, we describe the steps that led to the detection of these metabolites in the intracellular fraction of Sphingomonas sp. strain TTNP3. The formation of analogous intracellular metabolites resulting from the degradation of the technical mixture of NP is reported. To further elucidate these degradation products, studies were carried out with cells grown with 4(3',5'-dimethyl-3'-heptyl)-phenol as sole carbon source. The description of the syntheses of reference compounds, i.e. 4(3',5'-dimethyl-3'-heptyl)-resorcinol and 4(3',5'-dimethyl-3'-heptyl)-catechol and their comparative analyses with the intermediates of the degradation of 4(3',5'-dimethyl-3'-heptyl)-phenol are presented. |
| doi_str_mv | 10.1007/s10532-006-9058-6 |
| format | Article |
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F. X ; Meesters, R ; Mundt, M ; Schäffer, A ; Schmidt, B ; Schröder, H. -Fr ; Verstraete, W ; Vinken, R ; Hollender, J</creator><creatorcontrib>Corvini, P. F. X ; Meesters, R ; Mundt, M ; Schäffer, A ; Schmidt, B ; Schröder, H. -Fr ; Verstraete, W ; Vinken, R ; Hollender, J</creatorcontrib><description>Sphingomonas sp. strain TTNP3 has been previously described as a bacterium that is capable of degrading the technical mixture of nonylphenol (NP) isomers and also the 4(3',5'-dimethyl-3'-heptyl)-phenol single isomer of NP. Until recently, 3,5-dimethyl-3-heptanol was the only reported metabolite of 4(3',5'-dimethyl-3'-heptyl)-phenol. A short time ago, the detection of an intracellular metabolite resulting from the oxidation of 4(3',5'-dimethyl-3'-heptyl)-phenol which was identified as 2(3,5-dimethyl-3-heptyl)-benzenediol has been reported. A decisive element for this identification was the occurrence of some slight differences with the two most probable metabolites i.e. 4(3',5'-dimethyl-3'-heptyl)-resorcinol and 4(3',5'-dimethyl-3'-heptyl)-catechol. These facts led us to hypothesise some NIH shift mechanisms explaining the formation of 2(3',5'-dimethyl-3'-heptyl)-benzenediol. In the present work, we describe the steps that led to the detection of these metabolites in the intracellular fraction of Sphingomonas sp. strain TTNP3. The formation of analogous intracellular metabolites resulting from the degradation of the technical mixture of NP is reported. To further elucidate these degradation products, studies were carried out with cells grown with 4(3',5'-dimethyl-3'-heptyl)-phenol as sole carbon source. The description of the syntheses of reference compounds, i.e. 4(3',5'-dimethyl-3'-heptyl)-resorcinol and 4(3',5'-dimethyl-3'-heptyl)-catechol and their comparative analyses with the intermediates of the degradation of 4(3',5'-dimethyl-3'-heptyl)-phenol are presented.</description><identifier>ISSN: 0923-9820</identifier><identifier>EISSN: 1572-9729</identifier><identifier>DOI: 10.1007/s10532-006-9058-6</identifier><identifier>PMID: 16821104</identifier><language>eng</language><publisher>Dordrecht: Dordrecht : Kluwer Academic Publishers</publisher><subject>4(3',5'-Dimethyl-3'-heptyl)-phenol ; Bacteria ; Biodegradation of pollutants ; Biological and medical sciences ; Biotechnology ; Branched isomer ; Carbon sources ; Chromatography, High Pressure Liquid ; Degradation products ; Environment and pollution ; Fundamental and applied biological sciences. Psychology ; Gas Chromatography-Mass Spectrometry ; Industrial applications and implications. Economical aspects ; Magnetic Resonance Spectroscopy ; Metabolites ; Microbiology ; Nonylphenol ; Oxidation ; Oxidation-Reduction ; Phenols ; Phenols - analysis ; Phenols - metabolism ; Spectrometry, Mass, Electrospray Ionization ; Spectroscopy, Fourier Transform Infrared ; Sphingomonas ; Sphingomonas - chemistry ; Sphingomonas - metabolism ; Stereoisomerism</subject><ispartof>Biodegradation (Dordrecht), 2007-04, Vol.18 (2), p.233-245</ispartof><rights>2007 INIST-CNRS</rights><rights>Springer Science+Business Media B.V. 2007</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c411t-273194e00d8d17275e25663b3be9febce75a66a677f0b0583e289775b89ed7ee3</citedby><cites>FETCH-LOGICAL-c411t-273194e00d8d17275e25663b3be9febce75a66a677f0b0583e289775b89ed7ee3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18625686$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16821104$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Corvini, P. 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A short time ago, the detection of an intracellular metabolite resulting from the oxidation of 4(3',5'-dimethyl-3'-heptyl)-phenol which was identified as 2(3,5-dimethyl-3-heptyl)-benzenediol has been reported. A decisive element for this identification was the occurrence of some slight differences with the two most probable metabolites i.e. 4(3',5'-dimethyl-3'-heptyl)-resorcinol and 4(3',5'-dimethyl-3'-heptyl)-catechol. These facts led us to hypothesise some NIH shift mechanisms explaining the formation of 2(3',5'-dimethyl-3'-heptyl)-benzenediol. In the present work, we describe the steps that led to the detection of these metabolites in the intracellular fraction of Sphingomonas sp. strain TTNP3. The formation of analogous intracellular metabolites resulting from the degradation of the technical mixture of NP is reported. To further elucidate these degradation products, studies were carried out with cells grown with 4(3',5'-dimethyl-3'-heptyl)-phenol as sole carbon source. 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| ispartof | Biodegradation (Dordrecht), 2007-04, Vol.18 (2), p.233-245 |
| issn | 0923-9820 1572-9729 |
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| subjects | 4(3',5'-Dimethyl-3'-heptyl)-phenol Bacteria Biodegradation of pollutants Biological and medical sciences Biotechnology Branched isomer Carbon sources Chromatography, High Pressure Liquid Degradation products Environment and pollution Fundamental and applied biological sciences. Psychology Gas Chromatography-Mass Spectrometry Industrial applications and implications. Economical aspects Magnetic Resonance Spectroscopy Metabolites Microbiology Nonylphenol Oxidation Oxidation-Reduction Phenols Phenols - analysis Phenols - metabolism Spectrometry, Mass, Electrospray Ionization Spectroscopy, Fourier Transform Infrared Sphingomonas Sphingomonas - chemistry Sphingomonas - metabolism Stereoisomerism |
| title | Contribution to the Detection and Identification of Oxidation Metabolites of Nonylphenol in Sphingomonas sp. strain TTNP3 |
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