biostudies-literatureUnione LETN-ImmunoshapeMinisterio de Economía y CompetitividadETN-Tollerant3957-3965https://www.ebi.ac.uk/biostudies/studies/S-EPMC5484281biostudies-literatureUnknown23(16)We herein propose the use of fluoroacetamide and difluoroacetamide moieties as sensitive tags for the detection of sugar-protein interactions by simple ¹ H and/or ¹⁹ F NMR spectroscopy methods. In this process, we have chosen the binding of N,N'-diacetyl chitobiose, a ubiquitous disaccharide fragment in glycoproteins, by wheat-germ agglutinin (WGA), a model lectin. By using saturation-transfer difference (STD)-NMR spectroscopy, we experimentally demonstrate that, under solution conditions, the molecule that contained the CHF₂ CONH- moiety is the stronger aromatic binder, followed by the analogue with the CH₂ FCONH- group and the natural molecule (with the CH₃ CONH- fragment). In contrast, the molecule with the CF₃ CONH- isosChemistry (Weinheim an der Bergstrasse, Germany)Fluoroacetamide Moieties as NMR Spectroscopy Probes for the Molecular Recognition of GlcNAc-Containing Sugars: Modulation of the CH-π Stacking Interactions by Different Fluorination Patterns.PMC5484281642157642870CTQ2015-64597-C2-1PCTQ2015-64597-C2-P2CTQ2014-58779-RFranconetti ADiercks TCanada FJEcheverria BJimenez-Barbero JAlcala MSerna SReichardt NUnione LArda AfalseFluoroacetamide Moieties as NMR Spectroscopy Probes for the Molecular Recognition of GlcNAc-Containing Sugars: Modulation of the CH-π Stacking Interactions by Different Fluorination Patterns.We herein propose the use of fluoroacetamide and difluoroacetamide moieties as sensitive tags for the detection of sugar-protein interactions by simple ¹ H and/or ¹⁹ F NMR spectroscopy methods. In this process, we have chosen the binding of N,N'-diacetyl chitobiose, a ubiquitous disaccharide fragment in glycoproteins, by wheat-germ agglutinin (WGA), a model lectin. By using saturation-transfer difference (STD)-NMR spectroscopy, we experimentally demonstrate that, under solution conditions, the molecule that contained the CHF₂ CONH- moiety is the stronger aromatic binder, followed by the analogue with the CH₂ FCONH- group and the natural molecule (with the CH₃ CONH- fragment). In contrast, the molecule with the CF₃ CONH- isos2017-01-01T00:00:00Z2017 Mar2025-04-22T16:42:52.364Z2019-03-27T02:48:28ZS-EPMC54842812812479310.1002/chem.201605573