title: An efficient approach for conversion of 5-substituted 2-thiouridines built in RNA oligomers into corresponding desulfured 4-pyrimidinone products.
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.
authors.affiliation: Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Lodz, Poland.
authors.forename: Anna
authors.initials: A
authors.lastname: Chwialkowska
authors.affiliation: Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Lodz, Poland.
authors.forename: Ewelina
authors.initials: E
authors.lastname: Wielgus
authors.affiliation: Institute of Organic Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, Poland.
authors.forename: Grazyna
authors.initials: G
authors.lastname: Leszczynska
authors.affiliation: Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Lodz, Poland.
authors.forename: Milena
authors.initials: M
authors.lastname: Sobczak
authors.affiliation: Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Lodz, Poland.
authors.forename: Barbara
authors.initials: B
authors.lastname: Mikolajczyk
authors.affiliation: Institute of Organic Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, Poland.
authors.forename: Elzbieta
authors.initials: E
authors.lastname: Sochacka
authors.affiliation: Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Lodz, Poland. Electronic address: bnawrot@cbmm.lodz.pl.
authors.forename: Barbara
authors.initials: B
authors.lastname: Nawrot
mesh_terms: D009705:Nucleosides / Q000737:chemistry; D011744:Pyrimidinones / Q000737:chemistry*; D012313:RNA / Q000032:analysis / Q000138:chemical synthesis / Q000737:chemistry*; D012343:RNA, Transfer / Q000138:chemical synthesis / Q000737:chemistry; D060327:Solid-Phase Synthesis Techniques; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013464:Sulfuric Acids / Q000737:chemistry; D013696:Temperature; D013891:Thiouridine / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: C105273:2-thiouridine; D009705:Nucleosides; D011744:Pyrimidinones; D013464:Sulfuric Acids; D013891:Thiouridine; D012313:RNA; D012343:RNA, Transfer; C048813:potassium peroxymonosulfuric acid
keywords: 2-Thiouridine; Oxidative desulfuration; Oxidative stress; Oxone; tRNA