{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Unione L"],"funding":["ETN-Immunoshape","Ministerio de Economía y Competitividad","ETN-Tollerant"],"pagination":["3957-3965"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC5484281"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["23(16)"],"pubmed_abstract":["We herein propose the use of fluoroacetamide and difluoroacetamide moieties as sensitive tags for the detection of sugar-protein interactions by simple <sup>1</sup> H and/or <sup>19</sup> 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 CHF<sub>2</sub> CONH- moiety is the stronger aromatic binder, followed by the analogue with the CH<sub>2</sub> FCONH- group and the natural molecule (with the CH<sub>3</sub> CONH- fragment). In contrast, the molecule with the CF<sub>3</sub> CONH- isos"],"journal":["Chemistry (Weinheim an der Bergstrasse, Germany)"],"pubmed_title":["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."],"pmcid":["PMC5484281"],"funding_grant_id":["642157","642870","CTQ2015-64597-C2-1P","CTQ2015-64597-C2-P2","CTQ2014-58779-R"],"pubmed_authors":["Franconetti A","Diercks T","Canada FJ","Echeverria B","Jimenez-Barbero J","Alcala M","Serna S","Reichardt N","Unione L","Arda A"],"additional_accession":[]},"is_claimable":false,"name":"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.","description":"We herein propose the use of fluoroacetamide and difluoroacetamide moieties as sensitive tags for the detection of sugar-protein interactions by simple <sup>1</sup> H and/or <sup>19</sup> 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 CHF<sub>2</sub> CONH- moiety is the stronger aromatic binder, followed by the analogue with the CH<sub>2</sub> FCONH- group and the natural molecule (with the CH<sub>3</sub> CONH- fragment). In contrast, the molecule with the CF<sub>3</sub> CONH- isos","dates":{"release":"2017-01-01T00:00:00Z","publication":"2017 Mar","modification":"2025-04-22T16:42:52.364Z","creation":"2019-03-27T02:48:28Z"},"accession":"S-EPMC5484281","cross_references":{"pubmed":["28124793"],"doi":["10.1002/chem.201605573"]}}