Nucleic Acids Research, 1980, Vol. 8, No. 6 1421-1433
© 1980
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Nucleoside conformation is determined by the electronegativity of the sugar substituent
*Service de Biochimie, Bat. 142, Départment de Biologie CEN-Saclay, B.P.No. 2, F-91190 Gif-sur-Yvette, France
Department de Chimie, Université de Moncton Moncton, N-B, E1A 3E9, Canada
Received January 2, 1980. The proton and 13NMR spectra of uridine, deoxyuridine and four 2' substituted uridines (dUn, dUz, dUcl and dUf1) are reported. A linear relationship between the electronegativity of the 2'-substituent and the carbon-13 chemical shift of C2' is observed. Taking into account the effect of electronegativity by using the correction proposed by Karplus or by Jankowski, the proton-proton coupling constants have been used to compute the conformational equilibria of the six uridines. It is shown that the contribution of the N form (3'-endo -2'-exo) increases with the electronegativity of the 2' substituent. Thus dUfl contains some 85 % N form in solution. - Applying similar corrections to published data in the adenosine series, a similar correlation is observed. This observation, that the most polar substituent pulls the pucker to its side, holds also for 3'-substituted compounds, like cordycepin(3'dAdo) and 3'-deoxy-3'-amino-adenosine. It is suggested that the influence of the electronegativity could be the dominating effect in nucleoside conformations and would also hold for arabinosides and xylosides. This effect should therefore also be the principal force which determines the differences between DNA and RNA.
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