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
| Autor: | F. Javier Cañada, Niels C. Reichardt, Maria Alcalá, Begoña Echeverria, Antonio Franconetti, Luca Unione, Jesús Jiménez-Barbero, Tammo Diercks, Sonia Serna, Ana Ardá |
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| Rok vydání: | 2017 |
| Předmět: |
Magnetic Resonance Spectroscopy
Halogenation Wheat Germ Agglutinins Stereochemistry Fluoroacetates Disaccharide Stacking Chitobiose Disaccharides 010402 general chemistry 01 natural sciences Catalysis noncovalent interactions chemistry.chemical_compound NMR spectroscopy Molecular recognition fluorine Moiety Molecule Spectroscopy Triticum Full Paper molecular modeling 010405 organic chemistry Organic Chemistry General Chemistry Nuclear magnetic resonance spectroscopy Full Papers Microarray Analysis 0104 chemical sciences Protein–Carbohydrate Interactions | Hot Paper chemistry molecular recognition Protein Binding |
| Zdroj: | Chemistry (Weinheim an Der Bergstrasse, Germany) Chemistry-A European Journal |
| ISSN: | 0947-6539 |
| DOI: | 10.1002/chem.201605573 |
| Popis: | We herein propose the use of fluoroacetamide and difluoroacetamide moieties as sensitive tags for the detection of sugar–protein interactions by simple 1H and/or 19F 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 CHF2CONH‐ moiety is the stronger aromatic binder, followed by the analogue with the CH2FCONH‐ group and the natural molecule (with the CH3CONH‐ fragment). In contrast, the molecule with the CF3CONH‐ isoster displayed the weakest intermolecular interaction (one order of magnitude weaker). Because sugar–aromatic CH–π interactions are at the origin of these observations, these results further contribute to the characterization and exploration of these forces and offer an opportunity to use them to unravel complex recognition processes. |
| Databáze: | OpenAIRE |
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