Synthesis of 2′-hydrazine oligonucleotides and their efficient conjugation with aldehydes and 1,3-diketones

Timofei S. Zatsepin, Michael J. Gait, Tatiana S. Oretskaya, Dmitry A. Stetsenko

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

Oligodeoxyribonucleotides that contain a novel nucleoside, 2′-O-(2-hydrazinoethyl)uridine, were synthesised by NaBH3CN reduction of hydrazones formed from 2′-O-(2-oxoethyl)oligonucleotides with FmocNHNH2, followed by concd aq NH3 deprotection. The 2′-hydrazine oligonucleotides obtained were then used to synthesise a number of conjugates with aldehydes via hydrazone formation and with1,3-diketones via pyrazole formation. The method was shown to be applicable for the preparation of oligonucleotide-peptide conjugates.

Original languageEnglish
Pages (from-to)5515-5518
Number of pages4
JournalTetrahedron Letters
Volume47
Issue number31
DOIs
Publication statusPublished - 31 Jul 2006
Externally publishedYes

Keywords

  • 1,3-Diketone
  • Aldehyde
  • Conjugation
  • Hydrazone
  • Modified oligonucleotides
  • Pyrazole

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