Chemical Synthesis and Some Properties of 6-Substituted Flavins

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1980
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Kenney, William C.
Knappe, Wolfgang R.
McIntire, William
Singer, Thomas P.
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Biochemistry. 1980, 19(12), pp. 2538-2544. ISSN 0006-2960. eISSN 1520-4995. Available under: doi: 10.1021/bi00553a001
Zusammenfassung

A number of derivatives of riboflavin and of 3-methyllumiflavin substituted in the 6 position have been synthesized starting with 6-nitro flavins, reduction to the 6-amino flavin, and diazotization, followed by reaction with the appropriate nucleophile. The absorption spectra, oxidation-reduction potentials, and the electron spin resonance spectra of the radical cationic forms of several of these synthetic compounds have been determined, including 6-S-cysteinyl-3-methyllumiflavin and 6-S-cysteinylriboflavin. The latter has been shown to be identical with the dephosphorylated form of the aminoacyl flavin isolated from trimethylamine dehydrogenase [Steenkamp, D. J., Kenney, W . C., & Singer, T. P. (1978) J. Biol. Chem. 253, 2812-2817; Steenkamp, D. J., McIntire, W., & Kenney, W. C. (1978) J. Biol. Chem. 253, 2818-2824] in regard to absorption spectrum, photochemical properties, and mobility in high-voltage electrophoresis and in thin-layer chromatography. An unusually pronounced interaction between the amino group and the isoalloxazine ring system was deduced from the absorption spectra of 6-amino-3-methyllumiflavin and 6-aminoriboflavin.

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570 Biowissenschaften, Biologie
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ISO 690GHISLA, Sandro, William C. KENNEY, Wolfgang R. KNAPPE, William MCINTIRE, Thomas P. SINGER, 1980. Chemical Synthesis and Some Properties of 6-Substituted Flavins. In: Biochemistry. 1980, 19(12), pp. 2538-2544. ISSN 0006-2960. eISSN 1520-4995. Available under: doi: 10.1021/bi00553a001
BibTex
@article{Ghisla1980Chemi-8425,
  year={1980},
  doi={10.1021/bi00553a001},
  title={Chemical Synthesis and Some Properties of 6-Substituted Flavins},
  number={12},
  volume={19},
  issn={0006-2960},
  journal={Biochemistry},
  pages={2538--2544},
  author={Ghisla, Sandro and Kenney, William C. and Knappe, Wolfgang R. and McIntire, William and Singer, Thomas P.}
}
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