The missing link in linear alkylbenzenesulfonate surfactant degradation : 4-sulfoacetophenone as a transient intermediate in the degradation of 3-(4-sulfophenyl) butyrate by comamonas testosteroni KF-1

Lade...
Vorschaubild
Dateien
2010_aempdf_SPC_DS.pdf
2010_aempdf_SPC_DS.pdfGröße: 854.02 KBDownloads: 400
Datum
2010
Autor:innen
Netzer, Frederick von
Fleischmann, Thomas
Rentsch, Daniel
Kohler, Hans-Peter E.
Herausgeber:innen
Kontakt
ISSN der Zeitschrift
Electronic ISSN
ISBN
Bibliografische Daten
Verlag
Schriftenreihe
Auflagebezeichnung
ArXiv-ID
Internationale Patentnummer
Angaben zur Forschungsförderung
Projekt
Open Access-Veröffentlichung
Open Access Green
Sammlungen
Core Facility der Universität Konstanz
Gesperrt bis
Titel in einer weiteren Sprache
Forschungsvorhaben
Organisationseinheiten
Zeitschriftenheft
Publikationstyp
Zeitschriftenartikel
Publikationsstatus
Published
Erschienen in
Applied and environmental microbiology. 2010, 76(1), pp. 196-202. ISSN 0099-2240. eISSN 1098-5336. Available under: doi: 10.1128/AEM.02181-09
Zusammenfassung

Biodegradation of the laundry surfactant linear alkylbenzenesulfonate (LAS) involves complex bacterial communities. The known heterotrophic community has two tiers. First, all LAS congeners are oxygenated and oxidized to about 50 sulfophenylcarboxylates (SPC). Second, the SPCs are mineralized. Comamonas testosteroni KF-1 mineralizes 3-(4-sulfophenyl)butyrate (3-C4-SPC). During growth of strain KF-1 with 3-C4-SPC, two transient intermediates were detected in the culture medium. One intermediate was identified as 4-sulfoacetophenone (SAP) (4-acetylbenzenesulfonate) by nuclear magnetic resonance (NMR). The other was 4-sulfophenol (SP). This information allowed us to postulate a degradation pathway that comprises the removal of an acetyl moiety from (derivatized) 3-C4-SPC, followed by a Baeyer-Villiger monooxygenation of SAP and subsequent ester cleavage to yield SP. Inducible NADPH-dependent SAP-oxygenase was detected in crude extracts of strain KF-1. The enzyme reaction involved transient formation of 4-sulfophenol acetate (SPAc), which was completely hydrolyzed to SP and acetate. SP was subject to NADH-dependent oxygenation in crude extract, and 4-sulfocatechol (SC) was subject to oxygenolytic ring cleavage. The first complete degradative pathway for an SPC can now be depicted with 3-C4-SPC: transport, ligation to a coenzyme A (CoA) ester, and manipulation to allow abstraction of acetyl-CoA to yield SAP, Baeyer-Villiger monooxygenation to SPAc, hydrolysis of the ester to acetate and SP, monooxygenation of SP to SC, the ortho ring-cleavage pathway with desulfonation, and sulfite oxidation.

Zusammenfassung in einer weiteren Sprache
Fachgebiet (DDC)
570 Biowissenschaften, Biologie
Schlagwörter
Konferenz
Rezension
undefined / . - undefined, undefined
Zitieren
ISO 690SCHLEHECK, David, Frederick von NETZER, Thomas FLEISCHMANN, Daniel RENTSCH, Thomas HUHN, Alasdair M. COOK, Hans-Peter E. KOHLER, 2010. The missing link in linear alkylbenzenesulfonate surfactant degradation : 4-sulfoacetophenone as a transient intermediate in the degradation of 3-(4-sulfophenyl) butyrate by comamonas testosteroni KF-1. In: Applied and environmental microbiology. 2010, 76(1), pp. 196-202. ISSN 0099-2240. eISSN 1098-5336. Available under: doi: 10.1128/AEM.02181-09
BibTex
@article{Schleheck2010missi-8728,
  year={2010},
  doi={10.1128/AEM.02181-09},
  title={The missing link in linear alkylbenzenesulfonate surfactant degradation : 4-sulfoacetophenone as a transient intermediate in the degradation of 3-(4-sulfophenyl) butyrate by comamonas testosteroni KF-1},
  number={1},
  volume={76},
  issn={0099-2240},
  journal={Applied and environmental microbiology},
  pages={196--202},
  author={Schleheck, David and Netzer, Frederick von and Fleischmann, Thomas and Rentsch, Daniel and Huhn, Thomas and Cook, Alasdair M. and Kohler, Hans-Peter E.}
}
RDF
<rdf:RDF
    xmlns:dcterms="http://purl.org/dc/terms/"
    xmlns:dc="http://purl.org/dc/elements/1.1/"
    xmlns:rdf="http://www.w3.org/1999/02/22-rdf-syntax-ns#"
    xmlns:bibo="http://purl.org/ontology/bibo/"
    xmlns:dspace="http://digital-repositories.org/ontologies/dspace/0.1.0#"
    xmlns:foaf="http://xmlns.com/foaf/0.1/"
    xmlns:void="http://rdfs.org/ns/void#"
    xmlns:xsd="http://www.w3.org/2001/XMLSchema#" > 
  <rdf:Description rdf:about="https://kops.uni-konstanz.de/server/rdf/resource/123456789/8728">
    <dspace:isPartOfCollection rdf:resource="https://kops.uni-konstanz.de/server/rdf/resource/123456789/28"/>
    <foaf:homepage rdf:resource="http://localhost:8080/"/>
    <dc:contributor>Rentsch, Daniel</dc:contributor>
    <bibo:uri rdf:resource="http://kops.uni-konstanz.de/handle/123456789/8728"/>
    <dcterms:abstract xml:lang="eng">Biodegradation of the laundry surfactant linear alkylbenzenesulfonate (LAS) involves complex bacterial communities. The known heterotrophic community has two tiers. First, all LAS congeners are oxygenated and oxidized to about 50 sulfophenylcarboxylates (SPC). Second, the SPCs are mineralized. Comamonas testosteroni KF-1 mineralizes 3-(4-sulfophenyl)butyrate (3-C4-SPC). During growth of strain KF-1 with 3-C4-SPC, two transient intermediates were detected in the culture medium. One intermediate was identified as 4-sulfoacetophenone (SAP) (4-acetylbenzenesulfonate) by nuclear magnetic resonance (NMR). The other was 4-sulfophenol (SP). This information allowed us to postulate a degradation pathway that comprises the removal of an acetyl moiety from (derivatized) 3-C4-SPC, followed by a Baeyer-Villiger monooxygenation of SAP and subsequent ester cleavage to yield SP. Inducible NADPH-dependent SAP-oxygenase was detected in crude extracts of strain KF-1. The enzyme reaction involved transient formation of 4-sulfophenol acetate (SPAc), which was completely hydrolyzed to SP and acetate. SP was subject to NADH-dependent oxygenation in crude extract, and 4-sulfocatechol (SC) was subject to oxygenolytic ring cleavage. The first complete degradative pathway for an SPC can now be depicted with 3-C4-SPC: transport, ligation to a coenzyme A (CoA) ester, and manipulation to allow abstraction of acetyl-CoA to yield SAP, Baeyer-Villiger monooxygenation to SPAc, hydrolysis of the ester to acetate and SP, monooxygenation of SP to SC, the ortho ring-cleavage pathway with desulfonation, and sulfite oxidation.</dcterms:abstract>
    <dc:language>eng</dc:language>
    <dc:contributor>Huhn, Thomas</dc:contributor>
    <dc:creator>Netzer, Frederick von</dc:creator>
    <dcterms:available rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2011-03-24T17:46:01Z</dcterms:available>
    <dspace:hasBitstream rdf:resource="https://kops.uni-konstanz.de/bitstream/123456789/8728/1/2010_aempdf_SPC_DS.pdf"/>
    <dcterms:hasPart rdf:resource="https://kops.uni-konstanz.de/bitstream/123456789/8728/1/2010_aempdf_SPC_DS.pdf"/>
    <dcterms:bibliographicCitation>First publ. in: Applied and environmental microbiology 76 (2010), 1, pp. 196-202</dcterms:bibliographicCitation>
    <dc:rights>terms-of-use</dc:rights>
    <dcterms:title>The missing link in linear alkylbenzenesulfonate surfactant degradation : 4-sulfoacetophenone as a transient intermediate in the degradation of 3-(4-sulfophenyl) butyrate by comamonas testosteroni KF-1</dcterms:title>
    <dc:contributor>Kohler, Hans-Peter E.</dc:contributor>
    <dcterms:issued>2010</dcterms:issued>
    <dc:creator>Fleischmann, Thomas</dc:creator>
    <dc:creator>Huhn, Thomas</dc:creator>
    <dcterms:rights rdf:resource="https://rightsstatements.org/page/InC/1.0/"/>
    <dc:contributor>Schleheck, David</dc:contributor>
    <dc:creator>Rentsch, Daniel</dc:creator>
    <dc:date rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2011-03-24T17:46:01Z</dc:date>
    <dc:format>application/pdf</dc:format>
    <void:sparqlEndpoint rdf:resource="http://localhost/fuseki/dspace/sparql"/>
    <dc:creator>Schleheck, David</dc:creator>
    <dc:creator>Cook, Alasdair M.</dc:creator>
    <dc:contributor>Fleischmann, Thomas</dc:contributor>
    <dc:creator>Kohler, Hans-Peter E.</dc:creator>
    <dc:contributor>Netzer, Frederick von</dc:contributor>
    <dc:contributor>Cook, Alasdair M.</dc:contributor>
    <dcterms:isPartOf rdf:resource="https://kops.uni-konstanz.de/server/rdf/resource/123456789/28"/>
  </rdf:Description>
</rdf:RDF>
Interner Vermerk
xmlui.Submission.submit.DescribeStep.inputForms.label.kops_note_fromSubmitter
Kontakt
URL der Originalveröffentl.
Prüfdatum der URL
Prüfungsdatum der Dissertation
Finanzierungsart
Kommentar zur Publikation
Allianzlizenz
Corresponding Authors der Uni Konstanz vorhanden
Internationale Co-Autor:innen
Universitätsbibliographie
Ja
Begutachtet
Diese Publikation teilen