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Biomolecules 2015, 5(4), 3177-3192;

Fluorinated Carbohydrates as Lectin Ligands: 19F-Based Direct STD Monitoring for Detection of Anomeric Selectivity

Centre de Recherches sur les Macromolécules Végétales, UPR5301, CNRS-Université Grenoble Alpes, BP53, 38041 Grenoble cédex 09, France
CIC bioGUNE, Bizkaia Technological Park, Building 800, 48160 Derio, Spain
Ikerbasque, Basque Foundation for Science, 48013 Bilbao, Spain
Institut für Physiologische Chemie, Tierärztliche Fakultät der Ludwig-Maximilians-Universität, Veterinärstr. 13, 80539 München, Germany
Chemical and Physical Biology, Centro de Investigaciones Biológicas, CIB-CSIC, Ramiro de Maeztu 9, 28040 Madrid, Spain
Authors to whom correspondence should be addressed.
Academic Editor: Hans Vliegenthart
Received: 9 June 2015 / Revised: 2 November 2015 / Accepted: 4 November 2015 / Published: 13 November 2015
(This article belongs to the Special Issue Challenges in Glycan, Glycoprotein and Proteoglycan Research)
Full-Text   |   PDF [769 KB, uploaded 13 November 2015]   |  


The characterization of the binding of reducing carbohydrates present as mixtures of anomers in solution to a sugar recepor (lectin) poses severe difficulties. In this situation, NMR spectroscopy enables the observation of signals for each anomer in the mixture by applying approaches based on ligand observation. Saturation transfer difference (STD) NMR allows fast and efficient screening of compound mixtures for reactivity to a receptor. Owing to the exceptionally favorable properties of 19F in NMR spectroscopy and the often complex 1H spectra of carbohydrates, 19F-containing sugars have the potential to be turned into versatile sensors for recognition. Extending the recently established 1H → 1H STDre19F-NMR technique, we here demonstrate its applicability to measure anomeric selectivity of binding in a model system using the plant lectin concanavalin A (ConA) and 2-deoxy-2-fluoro-d-mannose. Indeed, it is also possible to account for the mutual inhibition between the anomers on binding to the lectin by means of a kinetic model. The monitoring of 19F-NMR signal perturbation disclosed the relative activities of the anomers in solution and thus enabled the calculation of their binding affinity towards ConA. The obtained data show a preference for the α anomer that increases with temperature. This experimental approach can be extended to others systems of biomedical interest by testing human lectins with suitably tailored glycan derivatives. View Full-Text
Keywords: agglutinin; carbohydrates; drug design; glycans; glycoproteins; lectins; sugar receptors agglutinin; carbohydrates; drug design; glycans; glycoproteins; lectins; sugar receptors

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Ribeiro, J.P.; Diercks, T.; Jiménez-Barbero, J.; André, S.; Gabius, H.-J.; Cañada, F.J. Fluorinated Carbohydrates as Lectin Ligands: 19F-Based Direct STD Monitoring for Detection of Anomeric Selectivity. Biomolecules 2015, 5, 3177-3192.

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