Aubert, Y ; Asseline, U
Organic & Biomolecular Chemistry 2 (23) 3496-3503
publié le , mis à jour le
We report here the synthesis of oligo-2’-deoxyribonucleotides (ODNs) conjugated with perylene. Introduction of perylene, coupled either directly or via a propyl linker to the anomeric position of a 2’-deoxyribose residue, induces the formation of two anomers. Single incorporations of each pure anomer of these sugar perylene units have been performed at either the 5’-end or an internal position of a pyrimidic pentadecamer. The binding properties of these modified ODNs with their single- and double-stranded DNA targets were studied by absorption spectroscopy. Double incorporations of the sugar perylene unit most efficient at stabilizing the triplex and duplex structures (the beta-anomer involving the propyl linker) have been performed at both the 5’-end and at an internal position (or both the 5’- and 3’-ends) of the ODN chain.