Synthesis and Properties of Modified Oligodeoxyribonucleotides Containing 2′-O-(2,3-Dihydroxypropyl)uridine and 2′-O-(2-Oxoethyl)uridine

T. S. Zatsepin, A. V. Kachalova, E. A. Romanova, D. A. Stetsenko, M. J. Gait, T. S. Oretskay

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

A new uridine derivative, 2′-O-(2,3-dihydroxypropyl)uridine, and its 3′-phosphoramidite were obtained for direct introduction into oligonucleotides during automated chemical synthesis. Oligonucleotides 10 to 15 nt long harboring 2′-O-(2,3-dihydroxypropyl)uridine residues were synthesized; periodate oxidation of these oligomers gave oligonucleotides containing 2′-O-(2-oxoethyl)uridine residues. The presence of a reactive aldehyde group in 2′ position of the carbohydrate moiety was confirmed by the interaction with p-nitrophenylhydrazine and methionine methyl ester. The thermostability of DNA duplexes containing modified units does not practically differ from that of the natural analogues.

Original languageEnglish
Pages (from-to)39-44
Number of pages6
JournalRussian Journal of Bioorganic Chemistry
Volume27
Issue number1
DOIs
Publication statusPublished - 2001
Externally publishedYes

Keywords

  • 2′-(O-2-oxoethyl)uridine
  • 2′-O-(2,3-dihydroxypropyl)uridine
  • Modified oligodeoxyribonucleotides

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