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

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 withp-nitrophenylhydrazine and methionine methyl ester. The thermostability of DNA duplexes containing modified units does not practically differ from that of the natural analogues.

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Zatsepin, T.S., Kachalova, A.V., Romanova, E.A. et al. Synthesis and Properties of Modified Oligodeoxyribonucleotides Containing 2"-O-(2,3-Dihydroxypropyl)uridine and 2"-O-(2-Oxoethyl)uridine. Russian Journal of Bioorganic Chemistry 27, 39–44 (2001). https://doi.org/10.1023/A:1009579002330

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  • DOI: https://doi.org/10.1023/A:1009579002330

  • modified oligodeoxyribonucleotides
  • 2"-O-(2
  • 3-dihydroxypropyl)uridine
  • 2"-(O-2-oxoethyl)uridine