Synthesis, Thermodynamic Properties, and Crystal Structure of RNA Oligonucleotides Containing 5-Hydroxymethylcytosine
| Autor: | Kossinova, Olga, Malygin, Alexey, Krol, Alain, Karpova, Galina, Riml, Christian, Lusser, Alexandra, Ennifar, Eric, Micura, Ronald |
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| Přispěvatelé: | Architecture et Réactivité de l'ARN (ARN), Institut de biologie moléculaire et cellulaire (IBMC), Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Institute of Chemical Biology and Fundamental Medicine, Siberian Branch of the Russian Academy of Sciences (SB RAS), Institute of Organic Chemistry, Center for Molecular Biosciences, Univ |
| Rok vydání: | 2017 |
| Předmět: |
Models
Molecular 0301 basic medicine Stereochemistry [SDV]Life Sciences [q-bio] Oligonucleotides Crystallography X-Ray Tetraloop 03 medical and health sciences chemistry.chemical_compound Carbohydrate Conformation [SDV.BBM]Life Sciences [q-bio]/Biochemistry Molecular Biology ComputingMilieux_MISCELLANEOUS Phosphoramidite Chemistry Oligonucleotide Organic Chemistry RNA [SDV.BBM.BM]Life Sciences [q-bio]/Biochemistry Molecular Biology/Molecular biology Nuclease protection assay Stem-loop 030104 developmental biology Biochemistry Duplex (building) 5-Methylcytosine Thermodynamics Cytosine |
| Zdroj: | Journal of Organic Chemistry Journal of Organic Chemistry, American Chemical Society, 2017, 82 (15), pp.7939-7945. ⟨10.1021/acs.joc.7b01171⟩ |
| ISSN: | 1520-6904 0022-3263 |
| Popis: | 5-Hydroxymethylcytosine (hm5C) is an RNA modification that has attracted significant interest because of the finding that RNA hydroxymethylation can favor mRNA translation. For insight into the mechanistic details of hm5C function to be obtained, the availability of RNAs containing this modification at defined positions that can be used for in vitro studies is highly desirable. In this work, we present an eight-step route to 5-hydroxymethylcytidine (hm5rC) phosphoramidite for solid-phase synthesis of modified RNA oligonucleotides. Furthermore, we examined the effects of hm5rC on RNA duplex stability and its impact on structure formation using the sarcin-ricin loop (SRL) motif. Thermal denaturation experiments revealed that hm5rC increases RNA duplex stability. By contrast, when cytosine within an UNCG tetraloop motif was replaced by hm5rC, the thermodynamic stability of the corresponding hairpin fold was attenuated. Importantly, incorporation of hm5rC into the SRL motif resulted in an RNA crystal structur... |
| Databáze: | OpenAIRE |
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