Synthesis and incorporation into DNA fragments of the artificial nucleobase, 2-amino-8-oxopurine.

Claudio Cadena-Amaro (1) , Muriel Delepierre (2) , Sylvie Pochet (1)

1 Chimie Organique
2 Résonance Magnétique Nucléaire des Biomolécules

The nucleoside 2-amino-9-(2-deoxy-beta-d-ribofuranosyl)-7,8-dihydro-8-oxo-purine (dJ) was obtained in eight steps from 2'-deoxyguanosine. The appropriate protected phosphoramidite was synthesized and incorporated into DNA oligonucleotides. The thermal stability of heteroduplexes containing 2-amino-8-oxopurine (J) was investigated by UV-thermal denaturation experiments. The results obtained can be interpreted by the base pairing schemes involving the two edges of dJ depending on the anti and syn orientations.

Claudio Cadena-Amaro, Muriel Delepierre, Sylvie Pochet. Synthesis and incorporation into DNA fragments of the artificial nucleobase, 2-amino-8-oxopurine.. Bioorganic and Medicinal Chemistry Letters, 2005, 15 (4), pp.1069-73. ⟨10.1016/j.bmcl.2004.12.021⟩. ⟨pasteur-00166211⟩