Synthesis and properties of oligodeoxyribonucleotides containing 2′-O-(2,3-dihydroxypropyl)- and 2′-O-(2-oxoethyl)arabinouridine residues

T. S. Zatsepin, Yu M. Ivanova, D. A. Stetsenko, M. J. Gait, T. S. Oretskaya

Research output: Contribution to journalArticlepeer-review

Abstract

2′-O-(2,3-Dihydroxypropyl)arabinouridine-containing oligodeoxyribonucleotides were synthesized starting from a new modified nucleoside, viz., 2′-O-(2,3-dihydroxypropyl)arabinouridine, and the corresponding 3′-phosphoramidite. Oxidation of these oligodeoxyribonucleotides with sodium periodate afforded oligonucleotides containing 2′-O-(2-oxoethyl)arabinouridine residues. Subsequent modification of the aldehyde-containing oligonucleotides involved the reactions with 9-hydrazinoacridine and N-aminooxyacetyl peptide and reductive amination by 4-(1-pyrenyl)butyrohydrazide and biotin hydrazide. Thermal stabilities of duplexes of modified oligodeoxyribonucleotides with complementary oligodeoxyribonucleotides are slightly lower than those of natural duplexes. Duplexes with complementary oligoribonucleotides are substantially destabilized.

Original languageEnglish
Pages (from-to)238-246
Number of pages9
JournalRussian Chemical Bulletin
Volume54
Issue number1
DOIs
Publication statusPublished - Jan 2005
Externally publishedYes

Keywords

  • Duplexes
  • Modified oligonucleotides

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