Synthesis and evaluation of an alkyne-modified ATP analog for enzymatic incorporation into RNA

Yuxuan Zheng, Peter A. Beal

Research output: Contribution to journalArticle

15 Scopus citations

Abstract

Alkyne-modified nucleoside analogs are useful for nucleic acid localization as well as functional and structural studies because of their ability to participate in copper-catalyzed azide/alkyne cycloaddition (CuAAC) reactions. Here we describe the synthesis of the triphosphate of 7-ethynyl-8-aza-7-deazaadenosine (7-EAATP) and the enzymatic incorporation of 7-EAA into RNA. The free nucleoside of 7-EAA is taken up by HeLa cells and incorporated into cellular RNA by endogenous RNA polymerases. In addition, 7-EAATP is a substrate for both T7 RNA polymerase and poly (A) polymerase from Escherichia coli in vitro, albeit at lower efficiencies than with ATP. This work adds to the toolbox of nucleoside analogs useful for RNA labeling.

Original languageEnglish (US)
Pages (from-to)1799-1802
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume26
Issue number7
DOIs
StatePublished - 2016

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Keywords

  • ATP analogs
  • Cellular RNA labeling
  • Click chemistry
  • Polyadenylation
  • T7 transcription

ASJC Scopus subject areas

  • Biochemistry
  • Clinical Biochemistry
  • Molecular Biology
  • Molecular Medicine
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

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