Synthesis of Trifluoromethylated Purine Ribonucleotides and Their Evaluation as ¹⁹F NMR Probes.

ABSTRACT: Protected guanosine and adenosine ribonucleosides and guanine nucleotides are readily functionalized with CF₃ substituents within the nucleobase. Protected guanosine is trifluoromethylated at the C8 position under radical-generating conditions in up to 95% yield and guanosine 5'-oligophosphates in up to 35% yield. In the case of adenosine, the selectivity of trifluoromethylation depends heavily on the functional group protection strategy and leads to a set of CF₃-modified nucleosides with different substitution patterns (C8, C2, or both) in up to 37% yield. Further transformations based on phosphorimidazolide chemistry afford various CF₃-substituted mono- and dinucleoside oligophosphates in good yields. The utility of the trifluoromethylated nucleotides as

SUBMITTER: Chrominski M 

PROVIDER: S-EPMC7497640 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature