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Synthesis of 5-fluoropyrimidine nucleotides as sensitive NMR probes of RNA structure

Academic Article
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Overview

authors

  • Hennig, M.
  • Scott, L. G.
  • Sperling, E.
  • Bermel, W.
  • Williamson, James

publication date

  • December 2007

journal

  • Journal of the American Chemical Society  Journal

abstract

  • Enzymatic synthesis methods for the fluorinated 5'-triphosphate analogues 5F-UTP and 5F-CTP have been developed to facilitate 19F-labeling of RNAs for biophysical studies. HIV-2 TAR RNAs were synthesized using these analogues by in vitro transcription reactions using T7 RNA polymerase. The uniform incorporation of 5F-U or 5F-C analogues into HIV-2 TAR RNA transcripts does not significantly alter the RNA structure or thermodynamic stability. Fluorine observed homonuclear 19F-19F and heteronuclear 19F-1H NOE experiments providing selective distance information are presented and discussed. The availability of efficient synthesis of 5F-UTP, and for the first time, 5F-CTP, will facilitate the use of 5F-labeled RNAs in structural, ligand binding, and dynamic studies of RNAs using the advantages of 19F-labeling.

subject areas

  • HIV Long Terminal Repeat
  • HIV-2
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Nucleic Acid Conformation
  • Nucleotides
  • Phosphates
  • Pyrimidines
  • RNA
  • RNA Probes
  • Sensitivity and Specificity
  • Temperature
  • Transition Temperature
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Identity

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja073825i

PubMed ID

  • 17990877
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Additional Document Info

start page

  • 14911

end page

  • 14921

volume

  • 129

issue

  • 48

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