3'-Fluoro-3'-deoxyribonucleoside 5'-triphosphates: synthesis and use as terminators of RNA biosynthesis

FEBS Lett. 1989 Jul 3;250(2):139-41. doi: 10.1016/0014-5793(89)80706-9.

Abstract

3'-Fluoro-3'-deoxy-uridine, -cytidine, -adenosine and -guanosine have been synthesized by glycosylation of the corresponding silylated bases with 1-O-acetyl-2,5-di-O-benzoyl-3-fluoro-3-deoxy-D-ribofuranose in the presence of Friedel-Crafts catalysts and were converted to the 5'-triphosphates, NTP(3'-F). It was shown that NTP(3'-F) are terminators of RNA synthesis catalyzed by DNA-dependent RNA polymerase from E. coli and may thus serve as tools for DNA sequencing.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Base Sequence
  • Catalysis
  • Chemical Phenomena
  • Chemistry
  • DNA-Directed DNA Polymerase / metabolism
  • Deoxyribonucleotides / chemical synthesis*
  • Deoxyribonucleotides / pharmacology
  • Electrophoresis, Agar Gel
  • Escherichia coli / enzymology
  • Molecular Sequence Data
  • RNA / antagonists & inhibitors
  • RNA / biosynthesis*

Substances

  • Deoxyribonucleotides
  • RNA
  • DNA-Directed DNA Polymerase