2′-Modified nucleosides for site-specific labeling of oligonucleotides

Elizabeth S. Krider, Jeremiah E. Miller, Thomas J. Meade*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

We report the synthesis of 2′-modified nucleosides designed specifically for incorporating labels into oligonucleotides. Conversion of these nucleosides to phosphoramidite and solid support-bound derivatives proceeds in good yield. Large-scale synthesis of 11-mer oligonucleotides possessing the 2′-modified nucleosides is achieved using these derivatives. Thermal denaturation studies indicate that the presence of 2′-modified nucleosides in 11-mer duplexes has minimal destabilizing effects on the duplex structure when the nucleosides are placed at the duplex termini. The powerful combination of phosphoramidite and support-bound derivatives of 2′-modified nucleosides affords the large-scale preparation of an entirely new class of oligonucleotides. The ability to synthesize oligonucleotides containing label attachment sites at 3′, intervening, and 5′ locations of a duplex is a significant advance in the development of oligonucleotide conjugates.

Original languageEnglish (US)
Pages (from-to)155-162
Number of pages8
JournalBioconjugate Chemistry
Volume13
Issue number1
DOIs
StatePublished - Feb 13 2002

ASJC Scopus subject areas

  • Biotechnology
  • Bioengineering
  • Biomedical Engineering
  • Pharmacology
  • Pharmaceutical Science
  • Organic Chemistry

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