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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Autor principal:	ALDERETE,JOEL B.
Lenguaje:	English
Publicado:	Sociedad Chilena de Química 2000
Materias:	AM1 cyclic nucleotides syn-anti equilibrium phosphodiesterases
Acceso en línea:	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0366-16442000000300004
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spelling	oai:scielo:S0366-164420000003000042001-03-23The Syn-Anti Equilibrium of Guanosine Cyclic 3',5'- Monophosphate and 8-Sustituted Derivatives: A Theoretical StudyALDERETE,JOEL B. AM1 cyclic nucleotides syn-anti equilibrium phosphodiesterases 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.info:eu-repo/semantics/openAccessSociedad Chilena de QuímicaBoletín de la Sociedad Chilena de Química v.45 n.3 20002000-09-01text/htmlhttp://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0366-16442000000300004en10.4067/S0366-16442000000300004
institution	Scielo Chile
collection	Scielo Chile
language	English
topic	AM1 cyclic nucleotides syn-anti equilibrium phosphodiesterases
spellingShingle	AM1 cyclic nucleotides syn-anti equilibrium phosphodiesterases ALDERETE,JOEL B. The Syn-Anti Equilibrium of Guanosine Cyclic 3',5'- Monophosphate and 8-Sustituted Derivatives: A Theoretical Study
description	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.
author	ALDERETE,JOEL B.
author_facet	ALDERETE,JOEL B.
author_sort	ALDERETE,JOEL B.
title	The Syn-Anti Equilibrium of Guanosine Cyclic 3',5'- Monophosphate and 8-Sustituted Derivatives: A Theoretical Study
title_short	The Syn-Anti Equilibrium of Guanosine Cyclic 3',5'- Monophosphate and 8-Sustituted Derivatives: A Theoretical Study
title_full	The Syn-Anti Equilibrium of Guanosine Cyclic 3',5'- Monophosphate and 8-Sustituted Derivatives: A Theoretical Study
title_fullStr	The Syn-Anti Equilibrium of Guanosine Cyclic 3',5'- Monophosphate and 8-Sustituted Derivatives: A Theoretical Study
title_full_unstemmed	The Syn-Anti Equilibrium of Guanosine Cyclic 3',5'- Monophosphate and 8-Sustituted Derivatives: A Theoretical Study
title_sort	syn-anti equilibrium of guanosine cyclic 3',5'- monophosphate and 8-sustituted derivatives: a theoretical study
publisher	Sociedad Chilena de Química
publishDate	2000
url	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0366-16442000000300004
work_keys_str_mv	AT alderetejoelb thesynantiequilibriumofguanosinecyclic35monophosphateand8sustitutedderivativesatheoreticalstudy AT alderetejoelb synantiequilibriumofguanosinecyclic35monophosphateand8sustitutedderivativesatheoreticalstudy
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The Syn-Anti Equilibrium of Guanosine Cyclic 3',5'- Monophosphate and 8-Sustituted Derivatives: A Theoretical Study

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