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Synthesis and Properties of Flavin Ribofuranosides and Flavin Ribopyranosides
Author(s) -
Schwögler Anja,
Gramlich Volker,
Carell Thomas
Publication year - 2000
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(20000906)83:9<2452::aid-hlca2452>3.0.co;2-6
Subject(s) - chemistry , nucleobase , flavin mononucleotide , rna , flavin group , oligonucleotide , glycosidic bond , stereochemistry , ribose , ribozyme , dna , cofactor , riboflavin , combinatorial chemistry , biochemistry , enzyme , gene
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.