@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}
}

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    <dcterms:title>Oxidation of 2-Thioflavins by Peroxides : formation of Flavin 2-S-Oxides</dcterms:title>
    <dc:creator>Massey, Vincent</dc:creator>
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    <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>
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    <dc:contributor>Massey, Vincent</dc:contributor>
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    <dc:creator>Ghisla, Sandro</dc:creator>
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    <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>
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    <dc:contributor>Hemmerich, Peter</dc:contributor>
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