An efficient approach for conversion of 5-substituted 2-thiouridines built in RNA oligomers into corresponding desulfured 4-pyrimidinone products
| Autor: | Barbara Nawrot, Milena Sobczak, Ewelina Wielgus, Barbara Mikołajczyk, Anna Chwialkowska, Grazyna Leszczynska, Elzbieta Sochacka |
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| Rok vydání: | 2015 |
| Předmět: |
Stereochemistry
Thiouridine Clinical Biochemistry Pharmaceutical Science Pyrimidinones Biochemistry RNA Transfer Drug Discovery Solid-Phase Synthesis Techniques Molecular Biology Phosphoramidite Chemistry Organic Chemistry Temperature RNA Nucleosides Sulfuric Acids Spectrometry Mass Matrix-Assisted Laser Desorption-Ionization Yield (chemistry) Transfer RNA Molecular Medicine Nucleoside Stoichiometry |
| Zdroj: | Bioorganic & Medicinal Chemistry Letters. 25:3100-3104 |
| ISSN: | 0960-894X |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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