[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].
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.
Ostrovskiĭ
V A
VA
Studentsov
E P
EP
Poplavskiĭ
V S
VS
Ivanov
N V
NV
Gurskaia
G V
GV
Zavodnik
V E
VE
Ias'ko
M V
MV
Semizarov
D G
DG
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
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