8-FIuoro-8-Demethylriboflavin as a Potential Active-Site-Directed Reagent for Flavoprotein. Reaction with Some Amino Acids1

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Abstract
8-FIuoro-8-demethylriboflavin was shown to be a potential active-site-directed reagent for flavoproteins. It reacted with the nucleophiles of N-acetylcysteine (-SH), N-acetyltyrosine (-OH), α-N-acetyllysine, and glycine (ε- and α-NH2) respectively) under fairly mild conditions, and the reaction products were identified. The reactivity of the fluorofiavin was higher than that of 8-chloro-8-demethylribo-flavin, which reacted only with the cysteine derivative among the amino acid derivatives used, and whose pseudo first order rate constant at 23°C was 1/23 of that of the fluorofiavin. The reactivity of the fluorofiavin was also estimated by 13C and 19F NMR spectroscopy. The results showed that this compound is more reactive than the chloroflavin.