Incorporation of the carbocyclic analogue of (E)-5-(2-bromovinyl)-2'-deoxyuridine 5'-triphosphate into a synthetic DNA

Biochem Biophys Res Commun. 1987 Sep 30;147(3):1105-12. doi: 10.1016/s0006-291x(87)80184-5.


The carbocyclic analogue of (E)-5-(2-bromovinyl)-2'-deoxyuridine, C-BVDU, is a very potent and selective anti-herpes-virus compound. In order to synthesize and study the properties of a DNA that contains C-BVDU, the 5'-triphosphate, C-BVDUTP was prepared and evaluated as a potential substrate of the E. coli Klenow DNA polymerase enzyme. Although C-BVDUTP proved to be a very poor substrate also of this enzyme, it could be incorporated up to 3.6% into the synthetic DNA, poly(dA-dT, C-BVDU). This level of substitution decreased significantly the template activity for DNA and RNA polymerases, as compared to that of poly(dA-dT).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bromodeoxyuridine / analogs & derivatives*
  • Chromatography, High Pressure Liquid
  • DNA / biosynthesis*
  • DNA Polymerase I / metabolism*
  • Deoxyuracil Nucleotides / metabolism*
  • Nucleic Acid Conformation
  • Nucleic Acid Denaturation
  • Peptide Fragments
  • Spectrum Analysis
  • Substrate Specificity
  • Templates, Genetic
  • Thymine Nucleotides / metabolism


  • Deoxyuracil Nucleotides
  • Peptide Fragments
  • Thymine Nucleotides
  • carbocyclic 5-(2-bromovinyl)-2'-deoxyuridine 5'-triphosphate
  • DNA
  • DNA Polymerase I
  • Bromodeoxyuridine
  • thymidine 5'-triphosphate