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Nucleic Acids Research, 1983, Vol. 11, No. 4 1167-1180
© 1983

CHEMISTRY

On the conformation of 5-substituted uridines as studied by proton magnetic resonance

Wolfgang Uhl*, Josef Reiner+ and Hans Gunter Gassen*

*lnstitut für Organische Chemie and Biochemie Technische Hochschule Darmstadt Petersenstrasse 22, D-6100 Darmstadt +Universnat Bayreuth/OCl Universitätsstrasse 30, D-8580 Bayreuth, FRG

Received November 29, 1982. Accepted January 18, 1983.

The proton magnetic resonance (pmr) spectra of 10 base–modified uridine derivatives x5Urd have been measured at 3°, 30°, and 60°C in order to correlate the electronic effects of different substituents with the molecular conformation of the respective nucleosides. The results presented demonstrate the close relation between conformational parameters and the electron–affinity of the substituents as reflected by their Hammett constants. Going from electron-donating to electron–acceptinq groups, the portion of N–conformer in the ribose N{leftrightharpoons}S equilibrium increases from 44% to about 90%. In addition the percentage of gauche–gauche rotamer as measured for the exocyclic groups changes from about 30% in nh1/2Urd to more than 80x0025; in no1/2Urd.


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