Synthesis of fluorinated indoles as RNA analogues.
Nucleoside analogues are chemical means to investigate hydrogen bonds, base stacking, and solvation as the three predominant forces that are responsible for the stability of secondary structure of nucleic acids. To obtain deeper insight into the contributions of these interactions to RNA stability apart from the ones exerted by the predominant nucleosides we decided to synthesize some novel nucleic acid analogues where the nucleobases are replaced by fluoroindoles. Fluorinated indoles can be compared to fluorinated benzimidazoles to determine the role of nitrogen in five membered ring system. The synthesis of fluoroindole ribonucleosides is described here.
Bozilović
Jelena
J
Institute for Organic Chemistry and Chemical Biology, Johann Wolfgang Goethe University, Frankfurt am Main, Germany.
Engels
Joachim W
JW
D001562:Benzimidazoles / Q000138:chemical synthesis / Q000737:chemistry; D054879:Halogenation; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D012313:RNA / Q000138:chemical synthesis* / Q000737:chemistry; D020871:RNA Stability; D012263:Ribonucleosides / Q000138:chemical synthesis* / Q000737:chemistry
D001562:Benzimidazoles; D007211:Indoles; D012263:Ribonucleosides; D012313:RNA