Publikation: Preparation and some properties of 6-substituted flavins as active site probes for flavin enzymes
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6-Azidoflavins, 6-thiocyanatoflavins, and 6-mercaptoflavins at the lumiflavin, riboflavin, FMN, and FAD level were prepared from the corresponding 6-aminoflavins and some of their properties investigated. They are bound tightly by apoflavin enzymes which bind either riboflavin, FMN, or FAD. 6-Azidoflavins undergo facile photolysis. One major product was identified as 6-aminoflavin. A further product, which was formed also during acid decomposition of the azide, results from opening of the flavin benzene ring and is proposed to have a lumazine structure. 6-Thiocyanatoflavins are easily converted by dithiothreitol to 6-mercaptoflavins. The latter are stabilized against dimerization in the presence of reducing thiols. 6-Mercaptoflavins have a pK of 5.9, which corresponds to ionization of the 6-SH function. The neutral form is yellow, while the anion is green, due to a long-wavelength band (λ, ~600 nm) extending beyond 700 nm. These properties suggest the use of these 6-substituted flavins for probing the active site of flavin enzymes. Because their reactive substituents are in close proximity to the flavin N(5)-position, these 6-substituted derivatives should also serve as useful probes of the environment around the flavin N(5), a position known to be involved in all flavin-mediated redox processes.
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GHISLA, Sandro, Vincent MASSEY, Kunio YAGI, 1986. Preparation and some properties of 6-substituted flavins as active site probes for flavin enzymes. In: Biochemistry. 1986, 25(11), pp. 3282-3289. ISSN 0006-2960. eISSN 1520-4995. Available under: doi: 10.1021/bi00359a030BibTex
@article{Ghisla1986Prepa-8412, year={1986}, doi={10.1021/bi00359a030}, title={Preparation and some properties of 6-substituted flavins as active site probes for flavin enzymes}, number={11}, volume={25}, issn={0006-2960}, journal={Biochemistry}, pages={3282--3289}, author={Ghisla, Sandro and Massey, Vincent and Yagi, Kunio} }
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