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Chiral Diaminopyrrolic Receptors for Selective Recognition of Mannosides. 2. A 3D view of the Recognition Modes by X-ray, NMR, and Molecular Modeling (Articolo in rivista)

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Chiral Diaminopyrrolic Receptors for Selective Recognition of Mannosides. 2. A 3D view of the Recognition Modes by X-ray, NMR, and Molecular Modeling (Articolo in rivista) (literal)

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A. Ardá, F. Javier Cañada, C. Nativi, O. Francesconi, G. Gabrielli, A. Ienco, J. Jiménez-Barbero, S. Roelens (2011)
Chiral Diaminopyrrolic Receptors for Selective Recognition of Mannosides. 2. A 3D view of the Recognition Modes by X-ray, NMR, and Molecular Modeling
in Chemistry - A European Journal
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A. Ardá, F. Javier Cañada, C. Nativi, O. Francesconi, G. Gabrielli, A. Ienco, J. Jiménez-Barbero, S. Roelens (literal)

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Centro de Investigaciones Biol?gicas (CSIC), Madrid, Spain; Dipartimento di Chimica, Universit?à di Firenze, Firenze, Italy; Istituto di Chimica dei Composti OrganoMetallici (ICCOM), Consiglio Nazionale delle Ricerche (CNR), Italy; Istituto di Metodologie Chimiche (IMC), Consiglio Nazionale delle Ricerche (CNR), Italy. (literal)

Titolo

Chiral Diaminopyrrolic Receptors for Selective Recognition of Mannosides. 2. A 3D view of the Recognition Modes by X-ray, NMR, and Molecular Modeling (literal)

Abstract

The structural features of a representative set of five complexes of octyl alpha- and beta-mannosides with some members of a new generation of chiral tripodal diaminopyrrolic receptors, namely, (R)-5 and (S)- and (R)-7, have been investigated in solution and in the solid state by a combined X-ray, NMR spectroscopy, and molecular modeling approach. In the solid state, the binding arms of the free receptors 7 delimit a cleft in which two solvent molecules are hydrogen bonded to the pyrrolic groups and to the benzenic scaffold. In a polar solvent (CD3CN), chemical shift and intermolecular NOE data, assisted by molecular modeling calculations, ascertained the binding modes of the interaction between the receptor and the glycoside for these complexes. Although a single binding mode was found to adequately describe the complex of the acyclic receptor 5 with the alpha-mannoside, for the complexes of the cyclic receptors 7 two different binding modes were required to simultaneously fit all the experimental data. In all cases, extensive binding through hydrogen bonding and CH-pi interactions is responsible for the affinities measured in the same solvent. Furthermore, the binding modes closely account for the recognition preferences observed toward the anomeric glycosides and for the peculiar enantiodiscrimination properties exhibited by the chiral receptors (literal)

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