2-Amino-α-2′-deoxyadenosine increased duplex stability of methoxyethylphosphoramidate α-Oligodeoxynucleotides with RNA target

A new efficient synthesis of 2-amino-α-2′-deoxyadenosine and its incorporation into methoxyethylphosphoramidate α-oligodeoxynucleotides (ODNs) via H-phosphonate chemistry were reported. Thermal denaturation experiments demonstrated a significant stabilization of the complexes formed between these analogues and their RNA target (+2 °C/NH2A) relative to adenosine-containing phosphoramidate α-oligonucleotides. Concerning the binding specificity of these modified ODNs, unlike natural ODNs, discrimination against G pairing is higher and against C pairing is lower.