Structural and Energetic Effects of O2'-Ribose Methylation of Protonated Pyrimidine Nucleosides.
2′-O-methyl-5-methyluridine (Thdm)
2′-O-methylation
2′-O-methylcytidine (Cydm)
2′-O-methyluridine (Urdm)
5-Methyluridine
Cytidine (Cyd)
Cytosine (Cyt)
Density functional theory (DFT)
Electronic structure calculations
Electrospray ionization (ESI)
Energy-resolved collision-induced dissociation (ER-CID)
Fourier transform ion cyclotron resonance mass spectrometer (FT-ICR MS)
Gas-phase conformation
Glycosidic bond stability
Hydrogen-bonding interactions
Hydrogen-stretching region
IR fingerprint region
IR spectrum
IRMPD spectrum
Infrared multiple photon dissociation (IRMPD) action spectroscopy
Nucleobase
Nucleobase orientation
Nucleoside
Nucleoside modification
Protonation
Pyrimidine nucleosides
Quadrupole ion trap mass spectrometer (QIT MS)
Simulated annealing
Sugar puckering
Survival yield analysis
Tandem mass spectrometry
Thymidine (Thd)
Thymine (Thy)
Uracil (Ura)
Uridine (Urd)
Journal
Journal of the American Society for Mass Spectrometry
ISSN: 1879-1123
Titre abrégé: J Am Soc Mass Spectrom
Pays: United States
ID NLM: 9010412
Informations de publication
Date de publication:
Nov 2019
Nov 2019
Historique:
received:
22
05
2019
accepted:
23
07
2019
revised:
18
07
2019
pubmed:
23
8
2019
medline:
1
5
2020
entrez:
23
8
2019
Statut:
ppublish
Résumé
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]
Identifiants
pubmed: 31435890
doi: 10.1007/s13361-019-02300-9
pii: 10.1007/s13361-019-02300-9
doi:
Substances chimiques
Gases
0
Protons
0
Pyrimidine Nucleosides
0
RNA
63231-63-0
Ribose
681HV46001
DNA
9007-49-2
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
2318-2334Subventions
Organisme : National Science Foundation
ID : OISE-0730072
Organisme : National Science Foundation
ID : OISE-1357787
Organisme : National Science Foundation
ID : DBI-0922819
Organisme : National Science Foundation
ID : CHE-1709789
Organisme : National Science Foundation
ID : CHE-1664618
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