2024-03-28T17:40:58Zhttp://digital.csic.es/dspace-oai/requestoai:digital.csic.es:10261/368082020-05-28T13:37:28Zcom_10261_38com_10261_5com_10261_41com_10261_1col_10261_291col_10261_294
Experimental Measurement of Carbohydrate–Aromatic Stacking in Water by Using a Dangling-Ended DNA Model System
Morales, Juan Carlos
Reina, José J.
Díaz-Contreras, Irene
Aviñó, Anna
Nieto, Pedro M.
Eritja Casadellà, Ramón
European Commission
Ministerio de Educación y Ciencia (España)
Carbohydrate-aromatic stacking
Carbohydrates
DNA
Molecular recognition
Stacking interactions
8 páginas, 3 figuras, 2 tablas, 2 esquemas
Protein–carbohydrate recognition is of fundamental importance for a large number of biological processes; carbohydrate–aromatic stacking is a widespread, but poorly understood, structural motif in this recognition. We describe, for the first time, the measurement of carbohydrate–aromatic interactions from their contribution to the stability of a dangling-ended DNA model system. We observe clear differences in the energetics of the interactions of several monosaccharides with a benzene moiety depending on the number of hydroxy groups, the stereochemistry, and the presence of a methyl group in the pyranose ring. A fucose–benzene pair is the most stabilizing of the studied series (−0.4 Kcal mol−1) and this interaction can be placed in the same range as other more studied interactions with aromatic residues of proteins, such as Phe–Phe, Phe–Met, or Phe–His. The noncovalent forces involved seem to be dispersion forces and nonconventional hydrogen bonds, whereas hydrophobic effects do not seem to drive the interaction.
We thank the Ministry of Science and Education for funding (grant no.: CTQ-2006-01123/BQU) and for a Ramón y Cajal contract (J.C.M.).
Peer reviewed
2011-06-14T13:04:28Z
2011-06-14T13:04:28Z
2008-07-21
artículo
http://purl.org/coar/resource_type/c_6501
Chemistry - a European Journal 14(26): 7828-7835 (2008)
0947-6539
http://hdl.handle.net/10261/36808
10.1002/chem.200800335
1521-3765
http://dx.doi.org/10.13039/501100000780
en
http://dx.doi.org/10.1002/chem.200800335
Sí
open
Wiley-VCH