A comparison of the conformations adopted by some 5-bromovinyl-2'-deoxyuridines and a correlation with their antiviral properties: An x-ray study

László Párkányi, Alajos Kálmán, Mátyás Czugler, Teréz Kovács, Richard T. Walker

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Abstract

Crystal structures of (Z)-5-(2-bromovinyl)-2'-deoxyuridine, 3', 5'-di-O-acetyl-(E)-5-(2-bromovinyl)-2'-deoxyuridine and 3', 5'-di-O-p-chlorobenzoyl-5-(2-dibromovinyl)-2'-deoxyuridine are compared with each other and with that of the most potent antiviral agent (E)-5-(2-bromovlnyl)-2'-deoxyuridine (E-BVDU) reported earlier. A comparison of the conformation of 3', 5'-di-O-acetyl-pyrimidine nucleoside structures in which intermolecular hydrogen bond network formation is minimized, with those of their parent compounds has shown that the greatest change in rotation about the glycosyl bond and in the sugar ring pucker is exhibited by E-BVDU. Upon acylation this molecule changes from C2'-endo/C3'-exo conformation to C3'-endo/C4'-exo conformation. The relevance of these structures upon the biological activity of the nucleosides and in particular to their ability to be a substrate for thymidine kinase is discussed.

Original languageEnglish
Pages (from-to)4111-4121
Number of pages11
JournalNucleic acids research
Volume15
Issue number10
DOIs
Publication statusPublished - May 26 1987

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ASJC Scopus subject areas

  • Genetics

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