A thorough experimental study of CH/π interactions in water: quantitative structure-stability relationships for carbohydrate/aromatic complexes

  1. Jiménez-Moreno, E. 6
  2. Jiménez-Osés, G. 4
  3. Gómez, A.M. 6
  4. Santana, A.G. 6
  5. Corzana, F. 4
  6. Bastida, A. 6
  7. Jiménez-Barbero, J. 3
  8. Asensio, J.L. 6
  1. 1 Basque Foundation for Science, Ikerbasque, Bilbao, Spain
  2. 2 Center for Cooperative Research in Biosciences (CIC-bioGUNE), Derio, Bizkaia, Spain
  3. 3 Centro de Investigaciones Biológicas
    info

    Centro de Investigaciones Biológicas

    Madrid, España

    ROR https://ror.org/04advdf21

  4. 4 Universidad de La Rioja
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    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

  5. 5 Institute of Biocomputation and Physics of Complex Systems (BIFI), University of Zaragoza, BIFI-IQFR (CSIC), Zaragoza, Spain
  6. 6 Instituto de Química Orgánica General
    info

    Instituto de Química Orgánica General

    Madrid, España

    ROR https://ror.org/05e0q7s59

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Revista:
Chemical Science

ISSN: 2041-6520

Año de publicación: 2015

Volumen: 6

Número: 11

Páginas: 6076-6085

Tipo: Artículo

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DOI: 10.1039/C5SC02108A SCOPUS: 2-s2.0-84944238673 WoS: WOS:000362977000004 GOOGLE SCHOLAR

Otras publicaciones en: Chemical Science

Repositorio institucional: lock_openAcceso abierto Editor

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Financiación Adicional RAMÓN Y CAJAL G.J.O.

2015/00062/001

Resumen

CH/π interactions play a key role in a large variety of molecular recognition processes of biological relevance. However, their origins and structural determinants in water remain poorly understood. In order to improve our comprehension of these important interaction modes, we have performed a quantitative experimental analysis of a large data set comprising 117 chemically diverse carbohydrate/aromatic stacking complexes, prepared through a dynamic combinatorial approach recently developed by our group. The obtained free energies provide a detailed picture of the structure-stability relationships that govern the association process, opening the door to the rational design of improved carbohydrate-based ligands or carbohydrate receptors. Moreover, this experimental data set, supported by quantum mechanical calculations, has contributed to the understanding of the main driving forces that promote complex formation, underlining the key role played by coulombic and solvophobic forces on the stabilization of these complexes. This represents the most quantitative and extensive experimental study reported so far for CH/π complexes in water. This journal is © The Royal Society of Chemistry.