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Intramolecular Cation-π Interactions As the Driving Force To Restrict the Conformation of Certain Nucleosides

AuthorsCasanova, Elena; Priego, Eva María ; Jimeno, M. Luisa ; Aguado, Leire ; Negri, Ana; Gago, Federico; Camarasa Rius, María José ; Pérez Pérez, María Jesús
Issue Date2009
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 75 (6) : 1974-1981 (2010)
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.
Publisher version (URL)http://dx.doi.org/10.1021/jo902677s
Appears in Collections:(CENQUIOR) Artículos
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