8alpha-hydroxyflavinmononucleotide and related compounds.

Abstract

2', 3', 4'-Triacetyl-FMN has been transformed by selective radical bromination into 2', 3', 4'-triacetyl-8alpha-bromo-FMN, and the following hydrolysis of the latter has afforded 8alpha-hydroxy-FMN. The presence of the hydroxy group in the 8alpha position of 8alpha-hydroxy-FMN is confirmed by its acetylation into 2', 3'-diacetyl-8alpha-acetoxyriboflavin-4', 5'-cyclophosphate. The absorption spectra of the synthesized compounds have shown the reduction of the extinction ratios of the first and second absorption maxima in comparison with the extinction of the same maxima for 8alpha-hydroxyriboflavin. Unlike FMN, fluorescence quenching for 8alpha-hydroxy-FMN has been found.