Labeling of prenylated nucleic acid by Ene-type fluorination under physiological condition

Abstract

Prenyl groups have been found in a wide range of molecules including proteins, nucleic acids and natural products. For instance, farnesyl and geranylgeranyl modifications have been identified in Ras super-family proteins date back to 1960s, playing significant roles in living organisms. Prenyl and geranyl modifications in nucleic acids have also been revealed in recent years. We report here a preparation of a wide range of fluorinated molecules (or molecules tagged by fluorescent dye) with Selectfluor as reagent under physiological condition through the mild Ene-type fluorination of prenylated molecules. We demonstrate that our method could be utilized in the study of direct detection of prenylated nucleic acids via fluorine NMR spectroscopy.