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Synthesis, conformation of 3- -3-deoxythymidine and its 5-derivatives Substrate properties of 3- -3-deoxythymidine 5-triphosphate

Ostrovskii, V.A.; Studentsov, E.P.; Poplavskii, V.S.; Ivanova, N.V.; Gurskaya, G.V.; Zavodnik, V.E.; Jasko, M.V.; Semizarov, D.G.; Krayevsky, A.A.

Nucleosides and Nucleotides 14(6): 1289-1300

1995

Accession: 033634491
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5'-O-Benzoyl-3'-(tetrazole-2"-yl)-3'-deoxythymidine and its 5"-substituted derivatives were obtained by the reaction of 5'-O-benzoyl-2, 3'-anhydrothymidine with triethylammonium salts of either tetrazole or 5-substituted tetrazoles. Debenzoylation of these compounds yielded 3'-(tetrazole-2"-yl)-3'-deoxythymidine and its 5"-derivatives. Structures of two of them were confirmed by X-ray analysis. Both 3'-(tetrazole-2"-yl)-3'-deoxythymidine and 3'-(5"-methyltetrazole-2"-yl)-3'-deoxythymidine have anti-conformation with respect to the glycosidic bond, and 2'-endo-3'-exo-conformation of the sugar residue with gauche+ orientation relative to the C4'-C5' bond. 3'-(Tetrazole-2"-yl))-3'-deoxythymidine 5'-triphosphate exhibited poor termination substrate properties towards avian myeloblastosis virus reverse transcriptase and did not serve as a substrate for other employed DNA polymerases.

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Related References

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