Preparation of an imidazole-conjugated oligonucleotide

Marc Beban, Paul S. Miller

Research output: Contribution to journalArticle

Abstract

Postsynthetic modification of an oligonucleotide with an imidazole functional group was achieved by formation of an amide bond between the functional group and a single 2'-amino-2'-deoxyuridine, d-aU, of the oligonucleotide. The succinimidyl ester of N-glutaryl-histamine was synthesized under anhydrous conditions and added to the oligonucleotide in an acetonitrile-containing buffer at pH 8.0. Formation of the conjugate was assayed by digestion with snake venom phosphodiesterase and bacterial alkaline phosphatase, followed by reversed-phase HPLC to resolve constituent nucleosides. The disappearance of a peak corresponding to d-aU and the appearance of a peak that coelutes with authentic 2'-(N-glutaryl-N'-histaminyl)-2'-deoxyuridine confirmed the formation of the conjugate. Imidazole-conjugated oligonucleotides may have utility as antisense agents capable of hydrolyzing RNA.

Original languageEnglish (US)
Pages (from-to)599-603
Number of pages5
JournalBioconjugate Chemistry
Volume11
Issue number4
DOIs
StatePublished - Jul 1 2000

ASJC Scopus subject areas

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

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