Journal
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume 25, Issue 16, Pages 3100-3104Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2015.06.019
Keywords
2-Thiouridine; Oxidative desulfuration; Oxidative stress; tRNA; Oxone
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Funding
- National Science Centre in Poland [UMO-2011/03/B/ST5/02669]
- statutory funds of Centre of Molecular and Macromolecular Studies of the Polish Academy of Sciences
- Lodz University of Technology, Poland
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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. (C) 2015 Elsevier Ltd. All rights reserved.
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