Strategies for the Synthesis of Fluorinated Nucleosides, Nucleotides and Oligonucleotides

Fluorinated nucleosides and oligonucleotides are of specific interest as probes for studying nucleic acids interaction, structures, biological transformations, and its biomedical applications. Among various modifications of oligonucleotides, fluorination of preformed nucleoside and/or nucleotides have recently gained attention owing to the unique properties of fluorine atoms imparting medicinal properties with respect to the small size, electronegativity, lipophilicity, and ability for stereochemical control. This review deals with synthetic protocols for selective fluorination either at sugar or base moiety in a preformed nucleosides, nucleotides and nucleic acids using specific fluorinating reagents.

Automated summary

Fluorinated nucleosides and oligonucleotides are widely used as probes for studying nucleic acid interactions, structures, transformations, and biomedical applications. The unique properties of fluorine atoms, such as small size, electronegativity, lipophilicity, and stereochemical control, have attracted attention for the fluorination of preformed nucleosides and/or nucleotides. This review discusses the synthetic protocols for selective fluorination of sugar or base moieties in preformed nucleosides, nucleotides, and nucleic acids using specific fluorinating reagents.