Synthesis and conformational studies of unnatural pyrimidine nucleosides

Ferenc Sztaricskai, Andrea Csorvási, András Horváth, Gyula Batta, Zoltán Dinya

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2 Citations (Scopus)

Abstract

Starting from 3,4-di-O-acetyl-L-rhamnal (6) and thymine (7) the unsaturated nucleosides 1-(2′,3′,6′-trideoxy-4′-O-acetyl-α-and β-L-erythro-hex-2′-enopyranosyl)-thymine (8a and 8b) were prepared in anomerically pure form. In solution 8a was shown to be present in the 5Ho and oH5 conformations, whereas the predominant conformation of 8b was 5Ho. Chemical transformation of 8a and 8b led to the saturated nucleosides 1-(2′3′,6′-trideoxy-α-and β-L-eryrthro-hexopyranosyl)thymine (10a and 10b, respectively), which were converted into 1-(4′-azido-2′,3′,4′,6′-tetradeoxy-α-and β-L-threohexopyranosyl)thymine (12a and 12b). Preliminary biological studies showed that 9b was inactive against the HIV-1 and HIV-2 viruses.

Original languageEnglish
Pages (from-to)1223-1233
Number of pages11
JournalJournal of Carbohydrate Chemistry
Volume19
Issue number9
DOIs
Publication statusPublished - Jan 1 2000

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ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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