Anja Schwögler

Synthesis and Properties of Flavin Ribofuranosides and Flavin Ribopyranosides

Ribose-containing coenzymes like flavin mononucleotide (FMN) can be considered to be fossils of a prebiotic RNA world in which RNA encoded genetic information and catalyzed chemical reactions. To investigate the catalytic and base-pairing properties of FMN-containing oligonucleotides, the two cyclic flavin β-D-ribosides 3 and 4 derived from riboflavin 2 were synthesized (Schemes 1 and 2). These are both constitutionally strongly related to the nucleobase uridine and should be able to participate as catalytically competent and informational nucleobases in DNA, RNA, and p-RNA. Ribofuranoside 3 was too unstable to be isolated, but ribopyranoside 4 had the required stability, β-D-configuration, and anti-conformation of the glycosidic bond.