An efficient approach for conversion of 5-substituted 2-thiouridines built in RNA oligomers into corresponding desulfured 4-pyrimidinone products

Bioorg Med Chem Lett. 2015 Aug 15;25(16):3100-4. doi: 10.1016/j.bmcl.2015.06.019. Epub 2015 Jun 12.

Abstract

An efficient approach for the desulfuration of C5-substituted 2-thiouridines (R5S2U) bound in the RNA chain exclusively to 4-pyrimidinone nucleoside (R5H2U)-containing RNA products is proposed. This post-synthetic transformation avoids the preparation of a suitably protected H2U phosphoramidite, which otherwise would be necessary for solid-phase synthesis of the modified RNA. Optimization of the desulfuration, which included reaction stoichiometry, time and temperature, allowed to transform a set of ten R5S2U-RNAs into their R5H2U-RNA congeners in ca. 90% yield.

Keywords: 2-Thiouridine; Oxidative desulfuration; Oxidative stress; Oxone; tRNA.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Nucleosides / chemistry
  • Pyrimidinones / chemistry*
  • RNA / analysis
  • RNA / chemical synthesis
  • RNA / chemistry*
  • RNA, Transfer / chemical synthesis
  • RNA, Transfer / chemistry
  • Solid-Phase Synthesis Techniques
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
  • Sulfuric Acids / chemistry
  • Temperature
  • Thiouridine / analogs & derivatives*
  • Thiouridine / chemistry

Substances

  • 2-thiouridine
  • Nucleosides
  • Pyrimidinones
  • Sulfuric Acids
  • Thiouridine
  • RNA
  • RNA, Transfer
  • potassium peroxymonosulfuric acid