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Nucleic Acids Research, 1974, Vol. 1, No. 6 803-807
© 1974

Articles

Nucleoside conformations. 15. Flexibility of natural pyrimidine nudeosides around the glycosidic bond.

Received May 6, 1974. The flexibility of pyrimidine nucleosides has been investigated by measuring their circular dichrotsm in hydvoalooholic solutions over a large temperature range (–100° to +40°C). It was observed that ß-Uridine (Vrd) and B-Cytidine (Cyd) showed a decrease of the main diahroic band of about 40 percent, while sterically hindered nuoleoeides ({alpha}-Vrd, ara-Uracile, 02–2' anhydro- Urd, 2'3'-O-isopropylidene-Urd) showed only small decreases. It is concluded that the flexibility of the glycosidic linkage in conjunction with the pseudo-rotation of the sugar residue is responsible for these changes; the thermodynamic values which can be deduced from these decreases are compatible with an oscillatory motion around the glycosidic bond, but exclude anti-syn transformations in pyrimidine nucleosides.


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