Chemical Synthesis and Some Properties of 6-Substituted Flavins

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GHISLA, Sandro, William C. KENNEY, Wolfgang R. KNAPPE, William MCINTIRE, Thomas P. SINGER, 1980. Chemical Synthesis and Some Properties of 6-Substituted Flavins. In: Biochemistry. 19(12), pp. 2538-2544. ISSN 0006-2960. eISSN 1520-4995. Available under: doi: 10.1021/bi00553a001

@article{Ghisla1980Chemi-8425, title={Chemical Synthesis and Some Properties of 6-Substituted Flavins}, year={1980}, doi={10.1021/bi00553a001}, 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.} }

application/pdf Knappe, Wolfgang R. 1980 Ghisla, Sandro Attribution-NonCommercial-NoDerivs 2.0 Generic Ghisla, Sandro Chemical Synthesis and Some Properties of 6-Substituted Flavins McIntire, William McIntire, William 2011-03-24T17:43:30Z First publ. in: Biochemistry 19 (1980), 12, pp. 2538-2544 Kenney, William C. Kenney, William C. eng Singer, Thomas P. Knappe, Wolfgang R. 2011-03-24T17:43:30Z Singer, Thomas P. 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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