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• W2055192015 abstract "The configuration and the conformation of α and β anomers of pyrazomycin, cytidine and pseudouridine in aqueous solution have been investigated by 1HNMR at 250 MHz. T1 proton relaxation measurements are an excellent method to determine the conformation of the base around the glycosidic linkage. Frequently, steric hindrance considerations can help to decide which conformations are possible in nucleoside anomer pairs. The proton-proton coupling constants indicate that the N conformer is largely predominant in the α anomers while the S conformer is particularly abundant in β-pyrazomycin. The steric hindrance is much larger for α than for β-nucleosides and change of a C-C to a C-N glycosidic bond reduces considerably the rotational possibilities of the base. The relaxation data show that α-cytidine adopts the anti conformation with ⋎ = 200° in good agreement with the crystal structure and with the sterical computations. In the other case, when the syn and anti conformations are sterically accessible, the orientation of the base may be completely different from one nucleoside to the other. It can be predicted neither from the crystal structure nor from comparisons with similar compounds. For α-pseudouridine the predominant orientation of the base (⋎ = 120°) is in the boundary of the syn-anti regions; for β-cytidine the syn (⋎ = 65°) and anti (⋎ = 215°) conformations are equiprobable at room temperature while β-pseudouridine shows the syn conformation with ⋎ = 40°, the smallest angle observed until now. There is no correlation between the NS and synanti ratios." @default.
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• W2055192015 date "1977-12-01" @default.
• W2055192015 modified "2023-10-13" @default.
• W2055192015 title "PMR-relaxation and steric computations give unequivocal nucleoside conformations" @default.
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• W2055192015 doi "https://doi.org/10.1016/0005-2787(77)90036-3" @default.
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