Journal article:
Properties of flavins where the 8-Methyl group is replaced by mercapto-Residues

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1979
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Moore, Edwin G.
Massey, Vincent
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Abstract
Sulfur functions in position 8 of the flavin nucleus give rise to new modified flavin derivatives, which should prove useful as probes of the flavin binding domains of flavoproteins. Here, we report on some properties of 8-nor-8-alkylmercaptoflavins and 8-nor-8-mercaptoflavin which are readily formed by nucleophilic displacement by alkylmercaptides or sulfide, with 8-nor-8-chloroflavins as starting material. The new flavins are characterized by extensive shifts in spectral properties, with very high extinction coefficients. 8-nor-8-mercaptoriboflavin is easily and reversibly converted to its (-S-S-) dimer. Oxidation of the sulfur group by peracids forms first sulfoxides and then sulfones, in which the characteristic usual flavin spectrum is regained. A comparison of 8-SR-8-nor-flavins with 8-OR-8-nor-flavins (Ghisla, S., and Mayhew, S. G. (1976) Eur. J. Biochem 63, 373-390) indicates that in both classes of compounds, optical properties, ionization constants, and oxidation-reduction potentials follow similar patterns.
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570 Biosciences, Biology
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Journal of Biological Chemistry ; 254 (1979), 17. - pp. 8173-8178
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ISO 690MOORE, Edwin G., Sandro GHISLA, Vincent MASSEY, 1979. Properties of flavins where the 8-Methyl group is replaced by mercapto-Residues. In: Journal of Biological Chemistry. 254(17), pp. 8173-8178
BibTex
@article{Moore1979Prope-8745,
  year={1979},
  title={Properties of flavins where the 8-Methyl group is replaced by mercapto-Residues},
  number={17},
  volume={254},
  journal={Journal of Biological Chemistry},
  pages={8173--8178},
  author={Moore, Edwin G. and Ghisla, Sandro and Massey, Vincent}
}
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    <dcterms:abstract xml:lang="eng">Sulfur functions in position 8 of the flavin nucleus give rise to new modified  flavin derivatives, which should prove useful as probes of the flavin binding domains of flavoproteins. Here, we report on some properties of 8-nor-8-alkylmercaptoflavins and 8-nor-8-mercaptoflavin which are readily formed by nucleophilic displacement by alkylmercaptides or sulfide, with 8-nor-8-chloroflavins as starting material. The new flavins are characterized by extensive shifts in spectral properties, with very high extinction coefficients. 8-nor-8-mercaptoriboflavin is easily and reversibly converted to its (-S-S-) dimer. Oxidation of the sulfur group by peracids forms first sulfoxides and then sulfones, in which the characteristic usual flavin spectrum is regained. A comparison of 8-SR-8-nor-flavins with 8-OR-8-nor-flavins (Ghisla, S., and Mayhew, S. G. (1976) Eur. J. Biochem 63, 373-390) indicates that in both classes of compounds, optical properties, ionization constants, and oxidation-reduction potentials follow similar patterns.</dcterms:abstract>
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