Synthesis and interaction with thymidylate synthase of 5'-dithiophosphate and 5'-fluorothiophosphate of thymidine.

  title={Synthesis and interaction with thymidylate synthase of 5'-dithiophosphate and 5'-fluorothiophosphate of thymidine.},
  author={B Gołos and Konrad Misiura and M Olesiak and Andrzej Okruszek and Wojciech J. Stec and Wojciech Rode},
  journal={Acta biochimica Polonica},
  volume={45 1},
Thymidine-5'-fluorothiophosphate, dTMP(S)-F, was synthesized by the oxathiaphospholane, and thymidine 5'-dithiophosphate, dTMPS2, by the dithiaphospholane, method. To estimate the role of 5'-phosphate group ionization in binding of pyrimidine nucleotides by thymidylate synthase, dTMP(S)-F was studied as an inhibitor of mouse tumour (L1210) enzyme, and its inhibitory properties were compared with those of dTMPS2, a close dTMP analogue. While dTMPS2 proved to be an inhibitor, competitive vs dUMP… Expand
Interaction of Thymidylate Synthase with the 5-Thiophosphates, 5-Dithiophosphates, 5-H-Phosphonates and 5-S-Thiosulfates of 2-Deoxyuridine, Thymidine and 5-Fluoro-2-Deoxyuridine
The pHdependence of enzyme timeindependent inhibition by FdUMP and FdUMPS was found to correlate with the difference in pKa values of the phosphate and thiophosphate groups, so that binding of dUMP and its analogs is limited by the phosphate secondary hydroxyl ionization. Expand


The synthesis of nucleoside 5'-O-(1,1-dithiotriphosphates).
The AZT and deoxyadenosine derivatives were found to be inhibitors of HIV reverse transcriptase and modest antivirial activity against HIV-1 and HIV-2 replication in CEM cells. Expand
Nucleotide activation of glycogen phosphorylase b occurs only when the nucleotide phosphate is in a dianionic form.
  • S. Withers, N. Madsen
  • Chemistry, Medicine
  • Biochemical and biophysical research communications
  • 1980
Findings are interpreted in terms of an absolute requirement of the nucleotide activatorsite in phosphorylase for a nucleotide with a dianionic phosphate for the proposed mechanism of activation. Expand
A facile access to nucleoside phosphorofluoridate, nucleoside phosphorofluoridothioate, and nucleoside phosphorofluoridodithioate monoesters
Abstract Oxidation of H-phosphonate, H-phosphonothioate, or H-phosphonodithioate monoesters with iodine in pyridine in the presence of trimethylsilyl chloride, followed by addition of triethylamineExpand