Isosteric Triphosphonate Analogues of dNTP: Synthesis and Substrate Properties toward Various DNA Polymerases

A. Yu. Skoblov1, A. N. Semenyuk2, A. M. Murabuldaev3, V. V. Sosunov4, L. S. Viktorova2 and Yu. S. Skoblov1 #

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1 Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, ul. Miklukho-Maklaya 16/10, Moscow, 117997, Russia;
2 Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, ul. Vavilova 32, Moscow, 117984, Russia;
3 OOO Vysokie Tekhnologii, Moscow, Russia;
4 GU Central Research Institute of Tuberculosis, Moscow, Russia

Received: June 19, 2006;  in final form: June 21, 2006

Abstract.  Isosteric triphosphonate derivatives of 2′,3′-dideoxy-2′,3′-didehydroadenosine and 3′-deoxy-2′,3′-didehydrothymidine and their β,γ-substituted analogues were synthesized. Their substrate properties toward a number of reverse transcriptases of the human immunodeficiency and avian myeloblastosis viruses, human DNA polymerases α and β, and the Klenow fragment of Escherichia coli DNA polymerase I were studied.

Key words:  isosteric analogues of dNTP; substrate properties; human DNA polymerases; HIV and avian myeloblastosis reverse transcriptasesKlenow fragment

Russian Journal of Bioorganic Chemistry 2007, 33(5): 488-498