Preparation and characterization of pyrene modified uridine derivatives as potential electron donors in RNA

• DOI: 10.1039/c8ob02246a
• Publication Date: 2018-09-27T10:35:00Z
• Authors: Jennifer Frommer; Beatrice Karg; Klaus Weisz; Sabine Müller
• Keywords: Characterization

Charge transfer across double stranded DNA was observed for the first time about 20 years ago, and ever since it has been subject of a large number studies. RNA hardly investigated in this regard, which not least is due to lack suitably functionalized ribonucleotide building blocks serve as electron sources upon incorporation into oligoribonucleotides. We have synthesized two uridine derivatives carrying pyrene or dimethylaminopyrene linked C5 nucleobase. The key successful synthesis adaptation Suzuki-Miyaura conditions coupling moiety with ribonucleoside. Final decoration pyrenylated nucleosides standard 5'-O- 2'-O-protecting groups subsequent 3'-O-phosphitylation delivered RNA. Spectroscopic analysis uridines accordingly modified oligonucleotides showed that particular dimethyaminopyrene nucleoside promising candidate an source charge transport