title: [3'-(Tetrazol-2''-yl-3'-deoxythymidine and its 5''-substituted form: synthesis and conformation in the crystalline state. Substrate properties of 3'-(tetrazol-2''-yl)-3'-deoxythymidine-5'-triphosphate in relation to DNA polymerases].
abstract: 5''-Derivatives of 3'-(tetrazole-2''-yl)-3'-deoxythymidines were synthesized by interaction of 5'-benzoyl-2',3'-anhydrothymidine with tetrazole or its 5-derivatives followed by debenzoylation. Structures of two of them, 3'-(tetrazole-2''-yl)-3'-deoxythymidine and 3'-(5''-methyltetrazole-2''-yl)-3'-deoxythymidine, elucidated by X-ray analysis, revealed anti conformation of thymine about the glycosidic bond and 2'-endo-3'-exo-conformation of the sugar residue with gauche+ orientation with respect to C4'-C5'-bond. 3'-(Tetrazole-2''-yl)-3'-deoxythymidine 5'-triphosphate demonstrated poor substrate properties for the avian myeloblastosis virus reverse transcriptase and none for several other DNA polymerases.
authors.forename: V A
authors.initials: VA
authors.lastname: Ostrovskiĭ
authors.forename: E P
authors.initials: EP
authors.lastname: Studentsov
authors.forename: V S
authors.initials: VS
authors.lastname: Poplavskiĭ
authors.forename: N V
authors.initials: NV
authors.lastname: Ivanov
authors.forename: G V
authors.initials: GV
authors.lastname: Gurskaia
authors.forename: V E
authors.initials: VE
authors.lastname: Zavodnik
authors.forename: M V
authors.initials: MV
authors.lastname: Ias'ko
authors.forename: D G
authors.initials: DG
authors.lastname: Semizarov
mesh_terms: D001483:Base Sequence; D018360:Crystallography, X-Ray; D004259:DNA-Directed DNA Polymerase / Q000378:metabolism*; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009838:Oligodeoxyribonucleotides; D013379:Substrate Specificity; D013936:Thymidine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D013942:Thymine Nucleotides / Q000737:chemistry* / Q000378:metabolism
chemical_list: C092982:3'-(tetrazol-2''-yl)-3'-deoxythymidine; C092983:3'-(tetrazol-2''-yl)-3'-deoxythymidine-5'-triphosphate; D009838:Oligodeoxyribonucleotides; D013942:Thymine Nucleotides; D004259:DNA-Directed DNA Polymerase; D013936:Thymidine