Structural and Energetic Effects of O2′-Ribose Methylation of Protonated Pyrimidine Nucleosides
| Autor: | M. T. Rodgers, Yanlong Zhu, Isabelle Compagnon, Philippe Maître, Baptiste Schindler, C. C. He, Christopher P. McNary, P. B. Armentrout, Lin Fan, Y.-w. Nei, Vincent Steinmetz, L. A. Hamlow |
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| Přispěvatelé: | Laboratoire de Chimie Physique D'Orsay (LCPO), Université Paris-Sud - Paris 11 (UP11)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut Lumière Matière [Villeurbanne] (ILM), Centre National de la Recherche Scientifique (CNRS)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon |
| Rok vydání: | 2019 |
| Předmět: |
Models
Molecular Spectrometry Mass Electrospray Ionization Pyrimidine Stereochemistry Ribose 010402 general chemistry 01 natural sciences Nucleobase chemistry.chemical_compound [CHIM.ANAL]Chemical Sciences/Analytical chemistry Structural Biology ComputingMilieux_MISCELLANEOUS Spectroscopy chemistry.chemical_classification 2'-O-methylation 010401 analytical chemistry RNA Glycosidic bond DNA DNA Methylation Pyrimidine Nucleosides 0104 chemical sciences chemistry 5-Methyluridine Gases Protons Nucleoside |
| Zdroj: | Journal of The American Society for Mass Spectrometry Journal of The American Society for Mass Spectrometry, Springer Verlag (Germany), 2019, 30 (11), pp.2318-2334. ⟨10.1007/s13361-019-02300-9⟩ |
| ISSN: | 1044-0305 |
| DOI: | 10.1007/s13361-019-02300-9 |
| Popis: | The 2'-substituents distinguish DNA from RNA nucleosides. 2'-O-methylation occurs naturally in RNA and plays important roles in biological processes. Such 2'-modifications may alter the hydrogen-bonding interactions of the nucleoside and thus may affect the conformations of the nucleoside in an RNA chain. Structures of the protonated 2'-O-methylated pyrimidine nucleosides were examined by infrared multiple photon dissociation (IRMPD) action spectroscopy, assisted by electronic structure calculations. The glycosidic bond stabilities of the protonated 2'-O-methylated pyrimidine nucleosides, [Nuom+H]+, were also examined and compared to their DNA and RNA nucleoside analogues via energy-resolved collision-induced dissociation (ER-CID). The preferred sites of protonation of the 2'-O-methylated pyrimidine nucleosides parallel their canonical DNA and RNA nucleoside analogues, [dNuo+H]+ and [Nuo+H]+, yet their nucleobase orientation and sugar puckering differ. The glycosidic bond stabilities of the protonated pyrimidine nucleosides follow the order: [dNuo+H]+ < [Nuo+H]+ < [Nuom+H]+. The slightly altered structures help explain the stabilization induced by 2'-O-methylation of the pyrimidine nucleosides. |
| Databáze: | OpenAIRE |
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