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

• Published in: Biochemical and biophysical research communications Vol. 147; no. 3; pp. 1105 - 1112
• Main Authors: Sági, J., De Clercq, E., Szemző, A., Csárnyi, Á., Kovács, T., Ötvös, L.
• Format: Journal Article
• Language: English
• Published: San Diego, CA Elsevier Inc 30.09.1987; Elsevier
• Subjects: Applied sciences; Bromodeoxyuridine - analogs & derivatives; Chromatography, High Pressure Liquid; Deoxyuracil Nucleotides - metabolism; DNA - biosynthesis; DNA Polymerase I - metabolism; Escherichia coli; Exact sciences and technology; Nucleic Acid Conformation; Nucleic Acid Denaturation; Other techniques and industries; Peptide Fragments; Spectrum Analysis; Substrate Specificity; Templates, Genetic; Thymine Nucleotides - metabolism; ( E)-5-(2-bromovinyl)-2′-deoxyuridine is abbreviated; as BVDU, its carbocyclic analogue as C-BVDU; The 5′-triphosphate derivatives are BVDUTP and C-BVDUTP, respectively
• ISSN: 0006-291X; 1090-2104
• 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).