Effect of ribose O(2′)-methylation on the conformation of nucleosides and nucleotides

Prusiner, P.; Yathindra, N.; Sundaralingam, M.

doi:10.1016/0005-2787(74)90325-6

Cited by 38 publications

(27 citation statements)

References 14 publications

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“…This result is in accordance with confor m ational energy calculations on 2'-0-m ethyladenosine by Prusiner et al [29]. Conformational changes induced by 2' O-m ethylation are observed only in nucleotides [30].…”

Section: ' An D 3' M O Dified Derivativessupporting

confidence: 79%

Ribose Conformations of Adenosine Analogs Modified at the 2', 3' or 5' Positions

Klimke

Cuno

Lüdemann

et al. 1979

Zeitschrift Für Naturforschung C

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The solution conformation of adenosine(β)ribosides modified at the 2′, 3′ or 5′ position is derived from the analysis of the HRNMR spectra of the ribose protons. The conformational equilibria of the furanoside rings are described by the two state N ↔ S model introduced by Altona and Sundaralingam. The new compounds studied are: 2′-thiobenzoyl-2′-deoxyadenosine, 3′-thio-3′-deoxyadenosine, 2′-chloro-2′-deoxyadenosine, 3′-chloro-3′-deoxyadenosine, 2′-bromo- 2′-deoxyadenosine, 3′-bromo-3′-deoxyadenosine, 2′-O-methyladenosine, 3′-O-methyl-adenosine, 2,-deoxy-3,-O-methyladenosine, 5′-amino-5′-deoxyadenosine, 5′-acido-5′-deoxyadenosine, and 5′-chloro-5′-deoxyadenosine. The emphasis in this work is to study systematically the influence of the different substituents upon the conformational equilibria of the sugar. It is found that any substitution at the 2′ position stabilizes the S-conformer. An even more pronounced stabilization of the A-conformer in the 3′ substituted analogs is observed. The equilibrium changes in these classes of compounds can neither be correlated quantitatively with electronegativity differences nor with sterical differences between the various substituents. Substitution at the 5′ position influences the N ↔ S equilibrium only slightly, but has significant effects upon the conformational preferences of the exocyclic 5′-CH2R3 group.

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Section: ' An D 3' M O Dified Derivativessupporting

confidence: 79%

Ribose Conformations of Adenosine Analogs Modified at the 2', 3' or 5' Positions

Klimke

Cuno

Lüdemann

et al. 1979

Zeitschrift Für Naturforschung C

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“…We therefore expect that this region would also be reduced or eliminated in the corresponding methylated 5'-nucleotide. The present calculations on 2'MeCyd differ from these earlier calculations on nucleosides and nucleotides, and from a recent conformation-a1 study of a methylated ribopurine by Prusiner et al,15 in that (a) all conformational angles were permitted to be simultaneously variable, and (b) an assessment was made of the probabilities of the various sugar puckerings. The C(2')-endo regions, (2E) and f23T), represent over 2/3 of the calculated statistical weights.…”

Section: Comparison With Previous Potential Studiescontrasting

confidence: 60%

Conformation of a rare nucleoside in the anti‐codon loop of tRNAs: Potential energy calculations for 2′‐O‐methyl cytidine

et al. 1975

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SynopsisThe classical potential energy of 2'-0-methyl cytidine was calculated using contributions from van der Waals', electrostatic, and torsional terms. All five conformational angles, namely x, *, the methoxy angles ml and m2 which are unique to 0'-methylated nucleosides, and the sugar pucker P were varied simultaneously, and the energy was minimized with respect to these parameters. An extensive search of conformation space was made, particularly with respect to the sugar pucker. At the predicted global minimum, x and Q are anti-gg, P is C(2')-endo-C(3')-ero, and the methyl group is staggered with respect to the sugar. This calculated minimum agrees very well with the recently determined crystal structure of 2'-O-methyl cytidine. Thus, 2'-O-methylation still permits the conformational regions of the common nucleosides to be adopted. However, we infer that the predicted C(2')-endo sugar pucker results from the added methyl group, since cytidine is C(3')-endo in the crystal, and the common ribopyrimidine nucleosides generally favor C(3')-endo.

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“…2′-O-Me is one of the RNA modifications that does not directly alter the Watson-Crick laws governing base pairing, making its contribution to RNA structure and function even more complex to anticipate. In addition to protecting RNA from hydrolytic cleavage, a well-known consequence of 2′-O-Me is the stabilization of the nucleotide conformation (i.e., the C3′-endo puckering of the ribose moiety), which is favored in RNA strands due to the OH group [55]. In addition, 2′-O-Me restricts the rotational freedom of 3′-phosphate, thus potentially restricting RNA strand conformation and flexibility.…”

Section: 2′-o-methylation Contribution To Ribosome Structure and Fmentioning

confidence: 99%

2′-O-Methylation of Ribosomal RNA: Towards an Epitranscriptomic Control of Translation?

et al. 2018

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Ribosomal RNA (rRNA) undergoes post-transcriptional modification of over 200 nucleotides, predominantly 2′-O-methylation (2′-O-Me). 2′-O-Methylation protects RNA from hydrolysis and modifies RNA strand flexibility but does not contribute to Watson-Crick base pairing. The contribution of 2′-O-Me to the translational capacity of ribosomes has been established. Yet, how 2′-O-Me participates in ribosome biogenesis and ribosome functioning remains unclear. The development of 2′-O-Me quantitative mapping methods has contributed to the demonstration that these modifications are not constitutive but rather provide heterogeneity to the ribosomal population. Moreover, recent advances in ribosome structure analysis and in vitro translation assays have proven, for the first time, that 2′-O-Me contributes to regulating protein synthesis. This review highlights the recent data exploring the impact of 2′-O-Me on ribosome structure and function, and the emerging idea that the rRNA epitranscriptome is involved in translational control.

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Effect of ribose O(2′)-methylation on the conformation of nucleosides and nucleotides

Cited by 38 publications

References 14 publications

Ribose Conformations of Adenosine Analogs Modified at the 2', 3' or 5' Positions

Ribose Conformations of Adenosine Analogs Modified at the 2', 3' or 5' Positions

Conformation of a rare nucleoside in the anti‐codon loop of tRNAs: Potential energy calculations for 2′‐O‐methyl cytidine

2′-O-Methylation of Ribosomal RNA: Towards an Epitranscriptomic Control of Translation?

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