The Syn-Anti Equilibrium of Guanosine Cyclic 3',5'- Monophosphate and 8-Sustituted Derivatives: A Theoretical Study
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 t...
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| Lenguaje: | English |
| Publicado: |
Sociedad Chilena de Química
2000
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| Acceso en línea: | http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0366-16442000000300004 |
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| Sumario: | 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. |
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