Oxidation of 2-Thioflavins by Peroxides : formation of Flavin 2-S-Oxides

Lade...
Vorschaubild
Datum
1983
Autor:innen
Biemann, Monika
Claiborne, Al
Massey, Vincent
Hemmerich, Peter
Herausgeber:innen
Kontakt
ISSN der Zeitschrift
Electronic ISSN
ISBN
Bibliografische Daten
Verlag
Schriftenreihe
Auflagebezeichnung
DOI (zitierfähiger Link)
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
Zusammenfassung

The reaction of 2-thioriboflavin (sulfur replacing the oxygen substituent at position 2α) with hydrogen peroxide at pH ~10 leads to a blue flavin (λmax = 565 nm)which was purified in stable, homogeneous form. Titrations of 2-thioflavins with m-chloroperoxybenzoic acid also yield the same blue flavins with consumption of 1 eq of peracid. Anaerobic reduction of the blue flavin by sodium dithionite requires 4e¯ eq, and leads to formation of 1,5-dihydro-2-thioflavin. Oxidation of the latter with O2 restores the original 2-thioflavin. pH titration of the blue flavin shows two pKa values of 2.4 and 6.6, with no apparent ionization in the pH range 8-11. These results suggest that the blue flavin is a flavin 2-S-oxide. The visible absorption spectra of l flavin 2-S-oxides show a pronounced dependence on solvent polarity. This property suggests that these flavin analogs may be useful hydrophilic/hydrophobic probes of flavoprotein active sites. Flavin 2-S-oxides can be oxidized further to the 2-sulfinate and 2-sulfonate analogs, some properties of which are described.

Zusammenfassung in einer weiteren Sprache
Fachgebiet (DDC)
570 Biowissenschaften, Biologie
Schlagwörter
Konferenz
Rezension
undefined / . - undefined, undefined
Zitieren
ISO 690BIEMANN, Monika, Al CLAIBORNE, Sandro GHISLA, Vincent MASSEY, Peter HEMMERICH, 1983. Oxidation of 2-Thioflavins by Peroxides : formation of Flavin 2-S-Oxides. In: Journal of Biological Chemistry. 1983, 258(9), pp. 5440-5448
BibTex
@article{Biemann1983Oxida-7118,
  year={1983},
  title={Oxidation of 2-Thioflavins by Peroxides : formation of Flavin 2-S-Oxides},
  number={9},
  volume={258},
  journal={Journal of Biological Chemistry},
  pages={5440--5448},
  author={Biemann, Monika and Claiborne, Al and Ghisla, Sandro and Massey, Vincent and Hemmerich, Peter}
}
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/123456789/7118">
    <dc:format>application/pdf</dc:format>
    <dcterms:hasPart rdf:resource="https://kops.uni-konstanz.de/bitstream/123456789/7118/1/J_Biol_Chem_1983_BiemannOxidation_of_2_thioflavins_by_peroxides.pdf"/>
    <dcterms:title>Oxidation of 2-Thioflavins by Peroxides : formation of Flavin 2-S-Oxides</dcterms:title>
    <dc:creator>Massey, Vincent</dc:creator>
    <foaf:homepage rdf:resource="http://localhost:8080/"/>
    <dc:creator>Claiborne, Al</dc:creator>
    <dc:creator>Biemann, Monika</dc:creator>
    <dc:contributor>Ghisla, Sandro</dc:contributor>
    <dcterms:issued>1983</dcterms:issued>
    <dc:creator>Hemmerich, Peter</dc:creator>
    <dcterms:abstract xml:lang="eng">The reaction of 2-thioriboflavin (sulfur replacing the oxygen substituent at position 2α) with hydrogen peroxide at pH ~10 leads to a blue flavin (λmax = 565 nm)which was purified in stable, homogeneous form. Titrations of 2-thioflavins with m-chloroperoxybenzoic acid also yield the same blue flavins with consumption of 1 eq of peracid. Anaerobic reduction of the blue flavin by sodium dithionite requires 4e¯ eq, and leads to formation of 1,5-dihydro-2-thioflavin. Oxidation of the latter with O2 restores the original 2-thioflavin. pH titration of the blue flavin shows two pKa values of 2.4 and 6.6, with no apparent ionization in the pH range 8-11. These results suggest that the blue flavin is a flavin 2-S-oxide. The visible absorption spectra of l flavin 2-S-oxides show a pronounced dependence on solvent polarity. This property suggests that these flavin analogs may be useful hydrophilic/hydrophobic probes of flavoprotein active sites. Flavin 2-S-oxides can be oxidized further to the 2-sulfinate and 2-sulfonate analogs, some properties of which are described.</dcterms:abstract>
    <dc:language>eng</dc:language>
    <dc:contributor>Massey, Vincent</dc:contributor>
    <dc:rights>Attribution-NonCommercial-NoDerivs 2.0 Generic</dc:rights>
    <dc:creator>Ghisla, Sandro</dc:creator>
    <dcterms:rights rdf:resource="http://creativecommons.org/licenses/by-nc-nd/2.0/"/>
    <dspace:hasBitstream rdf:resource="https://kops.uni-konstanz.de/bitstream/123456789/7118/1/J_Biol_Chem_1983_BiemannOxidation_of_2_thioflavins_by_peroxides.pdf"/>
    <void:sparqlEndpoint rdf:resource="http://localhost/fuseki/dspace/sparql"/>
    <dc:contributor>Claiborne, Al</dc:contributor>
    <dcterms:bibliographicCitation>First publ. in: Journal of Biological Chemistry 258 (1983), 9, pp. 5440-5448</dcterms:bibliographicCitation>
    <dc:contributor>Biemann, Monika</dc:contributor>
    <dspace:isPartOfCollection rdf:resource="https://kops.uni-konstanz.de/server/rdf/resource/123456789/28"/>
    <bibo:uri rdf:resource="http://kops.uni-konstanz.de/handle/123456789/7118"/>
    <dc:contributor>Hemmerich, Peter</dc:contributor>
    <dcterms:isPartOf rdf:resource="https://kops.uni-konstanz.de/server/rdf/resource/123456789/28"/>
    <dc:date rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2011-03-24T17:31:37Z</dc:date>
    <dcterms:available rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2011-03-24T17:31:37Z</dcterms:available>
  </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
Nein
Begutachtet
Diese Publikation teilen