Martínez, J. Daniel, Valverde, Pablo, Delgado, Sandra, Romanò, Cecilia, Linclau, Bruno, Reichardt, Niels C., Oscarson, Stefan, Ardá, Ana, Jiménez-Barbero, Jesús and Cañada, F. Javier (2019) Unraveling sugar binding modes to DC-SIGN by employing fluorinated carbohydrates. Molecules. (doi:10.3390/molecules24122337).
Abstract
A 19F-NMR-based method is employed to assess the binding preferences and interaction details of a library of synthetic fluorinated monosaccharides towards DC-SIGN, a lectin of biomedical interest, which is involved in different viral infections, including HIV and Ebola, and is able to recognize a variety of self- and non-self-glycans. The employed strategy allows not only to screen a mixture of compounds, but also to obtain valuable information on the specific sugar-protein interactions. The analysis of the data demonstrates that monosaccharides Fuc, Man, Glc and Gal are able to bind DC-SIGN, although with decreasing affinity. Moreover, a new binding mode between Man moieties and DC-SIGN, which might have biological implications, has also been detected for the first time. The combination of the 19F with standard 1H-STD-NMR data, assisted by MD simulations, permitted to successfully define this new binding epitope, in which Man coordinates a Ca2+ ion of the lectin CRD through the axial OH-2 and equatorial OH-3 groups, thus mimicking the Fuc/DC-SIGN binding architecture.
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