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


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BIEMANN, 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. 258(9), pp. 5440-5448

@article{Biemann1983Oxida-7118, title={Oxidation of 2-Thioflavins by Peroxides : formation of Flavin 2-S-Oxides}, year={1983}, 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 xmlns:rdf="http://www.w3.org/1999/02/22-rdf-syntax-ns#" xmlns:bibo="http://purl.org/ontology/bibo/" xmlns:dc="http://purl.org/dc/elements/1.1/" xmlns:dcterms="http://purl.org/dc/terms/" xmlns:xsd="http://www.w3.org/2001/XMLSchema#" > <rdf:Description rdf:about="https://kops.uni-konstanz.de/rdf/resource/123456789/7118"> <dc:contributor>Massey, Vincent</dc:contributor> <dc:contributor>Biemann, Monika</dc:contributor> <dc:creator>Claiborne, Al</dc:creator> <dc:creator>Massey, Vincent</dc:creator> <dc:language>eng</dc:language> <dc:contributor>Claiborne, Al</dc:contributor> <dc:date rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2011-03-24T17:31:37Z</dc:date> <dc:creator>Hemmerich, Peter</dc:creator> <dcterms:rights rdf:resource="https://creativecommons.org/licenses/by-nc-nd/2.0/legalcode"/> <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:creator>Biemann, Monika</dc:creator> <dc:rights>deposit-license</dc:rights> <bibo:uri rdf:resource="http://kops.uni-konstanz.de/handle/123456789/7118"/> <dcterms:issued>1983</dcterms:issued> <dcterms:available rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2011-03-24T17:31:37Z</dcterms:available> <dc:contributor>Ghisla, Sandro</dc:contributor> <dcterms:title>Oxidation of 2-Thioflavins by Peroxides : formation of Flavin 2-S-Oxides</dcterms:title> <dc:creator>Ghisla, Sandro</dc:creator> <dc:format>application/pdf</dc:format> <dcterms:bibliographicCitation>First publ. in: Journal of Biological Chemistry 258 (1983), 9, pp. 5440-5448</dcterms:bibliographicCitation> <dc:contributor>Hemmerich, Peter</dc:contributor> </rdf:Description> </rdf:RDF>

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