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Boletín de la Sociedad Chilena de Química

Print version ISSN 0366-1644


ALDERETE, JOEL B.. The Syn-Anti Equilibrium of Guanosine Cyclic 3',5'- Monophosphate and 8-Sustituted Derivatives: A Theoretical Study. Bol. Soc. Chil. Quím. [online]. 2000, vol.45, n.3, pp.355-362. ISSN 0366-1644.

ABSTRACT The syn-anti conformational equilibrium for a series of nine cyclic nucleotides was studied at semiempirical AM1 level. The AM1 results indicate that for guanosine cyclic 3',5'-monophosphate and their derivatives substituted at 8-position, the syn-conformers are more stable than the anti ones. For purine derivatives without an amino group at position 2, which participate in a hydrogen bonding with the axial oxygen of the phosphate group, the anti conformation is preferred. The AM1 results suggest that syn-anti equilibruim is a dominant factor for the binding of cyclic nucleotides to cyclic phosphodiesterases. Reinterpretation of experimental results for the competitive inhibition of c-GMP-stimulated phosphodiesterase was performed.

Keywords : AM1; cyclic nucleotides; syn-anti equilibrium; phosphodiesterases.

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