4’-AZA-3’5’-dihomothymidine and derivatives

Jean M.J. Tronchet, Mohammed Iznaden, Françoise Barbalat-Rey, Istvan Komaromi, Naz Dolatshahi

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18 Citations (Scopus)

Abstract

A series of 3’-branched 4’-azanucleoside analogues have been prepared. These compounds comprise three asymmetric atoms, two carbons and one nitrogen. They constitute nucleoside analogues imparted with a “flickering configuration”, the nitrogen inversion replacing a D-L epimerization of their natural congeners. The l’,3’-cis and 1,3’-trans isomers have been separated and their configuration established by 1H NMR and the X-ray diffraction structure of one crystalline example. The configurations of the frozen invertomers were assessed by low temperature 1H NMR experiments assisted by molecular mechanics simulations. None of these compounds exhibited any significant in vitro antiviral activity.

Original languageEnglish
Pages (from-to)1737-1758
Number of pages22
JournalNucleosides and Nucleotides
Volume14
Issue number8
DOIs
Publication statusPublished - Jan 1 1995

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ASJC Scopus subject areas

  • Biochemistry
  • Genetics

Cite this

Tronchet, J. M. J., Iznaden, M., Barbalat-Rey, F., Komaromi, I., & Dolatshahi, N. (1995). 4’-AZA-3’5’-dihomothymidine and derivatives. Nucleosides and Nucleotides, 14(8), 1737-1758. https://doi.org/10.1080/15257779508009754