Crystal structure of O4-methyl uridine: stacking induced changes in the geometry of the pyrimidine ring and its mutagenic role.
The geometric properties of the pyrimidine ring of O4-methyl uridine more closely resemble those of cytidine than diketo uridine. Differences between the independent molecules of O4-methyl uridine are observed in the C(7)-O(4)-C(4)-C(5)-C(6) bond orders and the planarity of the pyrimidine rings. These differences are attributed to the monopole-induced dipole interactions between the ribose ring oxygen atom and a neighboring base of molecule A. A survey of the literature reveals that similar stacking-induced effects occur in other structures, involving both pyrimidine and purines. Finally, two base pairing schemes between O4-methyl uridine and guanosine, in which two hydrogen bonds can form, have been presented. Of these two the mispair with Watson-Crick geometry is favored.
D004563:Electrochemistry; D008745:Methylation; D008968:Molecular Conformation; D015394:Molecular Structure; D009153:Mutagens; D011743:Pyrimidines; D013329:Structure-Activity Relationship; D014529:Uridine / Q000031:analogs & derivatives* / Q000494:pharmacology
D009153:Mutagens; D011743:Pyrimidines; C063023:O(4)-methyluridine; C030986:pyrimidine; D014529:Uridine