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dc.contributor.authorCasanova, Elena-
dc.contributor.authorPriego, Eva María-
dc.contributor.authorJimeno, M. Luisa-
dc.contributor.authorAguado, Leire-
dc.contributor.authorNegri, Ana-
dc.contributor.authorGago, Federico-
dc.contributor.authorCamarasa Rius, María José-
dc.contributor.authorPérez Pérez, María Jesús-
dc.identifier.citationJournal of Organic Chemistry 75 (6) : 1974-1981 (2010)es_ES
dc.description.abstractDespite the well-established importance of intermolecular cation-π interactions in molecular recognition, intramolecular cation-π interactions have been less studied. Here we describe how the simultaneous presence of an aromatic ring at the 50-position of an inosine derivative and a positively charged imidazolium ring in the purine base drive the conformation of the nucleoside toward a very major conformer in solution that is stabilized by an intramolecular cation-π interaction. Therefore, the cation-π interaction between imidazolium ions and aromatic rings can also be proposed in the design of small molecules where this type of interaction is desirable. The imidazolium ion can be obtainedbya simple acidification of the pH of the media. So a simple change in pHcan shiftthe conformationalequilibrium from arandom to arestricted conformation stabilized by an intramolecular cation-π interaction. Thus the here described nucleosides can be considered as a new class of pH-dependent conformationally switchable molecules.es_ES
dc.description.sponsorshipThis research was supported by grants from the Spanish CICYT [SAF2006-12713-C02] and the Comunidad de Madrid [BIPEDD-CM, S-BIO/0214/2006]. E.C. thanks the Comunidad de Madrid and the Fondo Social Europeo (FSE) for a predoctoral fellowship. E-M.P. has a CSIC contract from the I3P programme financed by the FSE. L.A. thanks the Spanish Ministerio de Educaci on y Ciencia for a FPU predoctoral fellowship.es_ES
dc.publisherAmerican Chemical Societyes_ES
dc.titleIntramolecular Cation-π Interactions As the Driving Force To Restrict the Conformation of Certain Nucleosideses_ES
dc.description.peerreviewedPeer reviewedes_ES
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