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

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1983
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Biemann, Monika
Claiborne, Al
Massey, Vincent
Hemmerich, Peter
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Journal of Biological Chemistry. 1983, 258(9), pp. 5440-5448
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.

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570 Biowissenschaften, Biologie
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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}
}
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    <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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