The synthesis and hybridization properties of an oligonucleotide containing hexafluoroacetone ketal internucleotide linkages

Article abstract of DOI:10.1016/S0040-4039(96)02005-9

The hexafluoroketal functionality is isosteric with the phosphate linkage in DNA and RNA. A thymidine:thymidine dimer bearing a hexfluoroacetone ketal internucleolide linkage has been synthesized from hexafluoroacetone using a Mitsunobu reaction. The resulting dimer has been incorporated into an oligonucleotide and has been shown to result in poorer binding to a complementary DNA and RNA relative to an unmodified control.