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The electronic nature of the aglycone dictates the drive of the pseudorotational equilibrium of the pentofuranose moiety in C-nucleosides

We herein show for the first time that the specific electronic character of a C-aglycone dictates the thermodynamic preference of the two-state N S pseudorotational equilibrium to either N- or S-type sugar. As the electron-deficiency of the C-aglycone increases, a more favourable O4'(n) σ*(C1'-C(sp2)) interaction results into anomeric stabilization as indicated by more positive ∆H° for the drive of the N S equilibrium to more N-type sugar conformation with pseudoaxial aglycone. Alternatively, as the C-aglycone becomes more electron-rich, an unfavourable O4'(n) σ*(C1'-C(sp2)) interaction results into anomeric destabilization as indicated by more negative ∆H° for the drive of the N S equilibrium to more S-type sugar conformation with pseudoequatorial aglycone.