Oligonucleotides containing 2′-O-[2-(2,3-dihydroxypropyl)amino-2- oxoethyl]uridine as suitable precursors of 2′-aldehyde oligonucleotides for chemoselective ligation

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

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)

Abstract

2′-O-[2-(2,3-Diacetoxypropyl)amino-2-oxoethyl]uridine 3′-phosphoramidite was prepared and used in solid-phase synthesis to obtain oligonucleotides containing a 1,2-diol group, which may then be converted into a 2′-aldehyde group. The oligonucleotides were conjugated efficiently to various molecules by chemoselective ligation that involves an addition-elimination reaction between the 2′-aldehyde group and a suitable nucleophile, such as a hydrazine, a O-alkylhydroxylamine or an 1,2-aminothiol. The method was applied successfully to the conjugation of peptides to oligonucleotides at the 2′-position.

Original languageEnglish
Pages (from-to)4912-4920
Number of pages9
JournalBioorganic and Medicinal Chemistry
Volume13
Issue number16
DOIs
Publication statusPublished - 15 Aug 2005
Externally publishedYes

Keywords

  • Aldehyde
  • Conjugate
  • Hydrazine
  • Oligonucleotide
  • Oxime

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