Synthesis, structure and properties of daunomycin oligonucleotide derivatives

T. S. Godovikova, V. F. Zarytova, S. G. Lokhov, T. V. Maltseva, D. S. Sergeev

Institute of Bioorganic Chemistry, Siberian Division, Academy of Sciences of the USSR Novosibirsk

Abstract: Daunomycin derivatives of pT(DT) and oligodeoxynucleotides were synthesized using reactive zwitter-ionic 4-N,N-dimethylaminopyridine derivatives of the terminal phosphate group. Daunomycin oligodeoxynucleotide analogues form more stable complementary complexes than the corresponding non-modified oligonucleotides. Both one-and two-dimensional (2D NOESY and 2D COSY) NMR spectra of DT were recorded and the proton signals assigned. From the detected cross-relaxation between H6 of thymidine and HI', H2', H2" of the carbohydrate residue of daunomycin it was concluded that, in DMSO, the DT molecule has a rather stable conformation, apparently due to the stacking interaction between the mononucleotide and daunomycin residues.

Russian Journal of Bioorganic Chemistry 1990, 16 (10):1369-1378

Full Text (PDF, in Russian)