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.

ABSTRACT: 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- isos

SUBMITTER: Unione L 

PROVIDER: S-EPMC5484281 | biostudies-literature | 2017 Mar

REPOSITORIES: biostudies-literature