[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]

Bioorg Khim. 1995 Jan;21(1):49-54.
[Article in Russian]

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.

Publication types

  • English Abstract

MeSH terms

  • Base Sequence
  • Crystallography, X-Ray
  • DNA-Directed DNA Polymerase / metabolism*
  • Molecular Sequence Data
  • Molecular Structure
  • Oligodeoxyribonucleotides
  • Substrate Specificity
  • Thymidine / analogs & derivatives*
  • Thymidine / chemistry
  • Thymidine / metabolism
  • Thymine Nucleotides / chemistry*
  • Thymine Nucleotides / metabolism

Substances

  • 3'-(tetrazol-2''-yl)-3'-deoxythymidine
  • 3'-(tetrazol-2''-yl)-3'-deoxythymidine-5'-triphosphate
  • Oligodeoxyribonucleotides
  • Thymine Nucleotides
  • DNA-Directed DNA Polymerase
  • Thymidine