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© Institut Pasteur / Alban Orsini
Le bâtiment Nocard qui abrite le microscope Titan KriosTM, à l'Institut Pasteur (Paris)
Publication : The Journal of organic chemistry

Fluorinated Carbohydrates as Lectin Ligands: Simultaneous Screening of a Monosaccharide Library and Chemical Mapping by 19F NMR Spectroscopy.

Scientific Fields
Diseases
Organisms
Applications
Technique

Published in The Journal of organic chemistry - 18 Dec 2020

Martínez JD, Manzano AI, Calviño E, Diego A, Rodriguez de Francisco B, Romanò C, Oscarson S, Millet O, Gabius HJ, Jiménez-Barbero J, Cañada FJ,

Link to Pubmed [PMID] – 33258593

Link to DOI – 10.1021/acs.joc.0c01830

J Org Chem 2020 12; 85(24): 16072-16081

Molecular recognition of carbohydrates is a key step in essential biological processes. Carbohydrate receptors can distinguish monosaccharides even if they only differ in a single aspect of the orientation of the hydroxyl groups or harbor subtle chemical modifications. Hydroxyl-by-fluorine substitution has proven its merits for chemically mapping the importance of hydroxyl groups in carbohydrate-receptor interactions. 19F NMR spectroscopy could thus be adapted to allow contact mapping together with screening in compound mixtures. Using a library of fluorinated glucose (Glc), mannose (Man), and galactose (Gal) derived by systematically exchanging every hydroxyl group by a fluorine atom, we developed a strategy combining chemical mapping and 19F NMR T2 filtering-based screening. By testing this strategy on the proof-of-principle level with a library of 13 fluorinated monosaccharides to a set of three carbohydrate receptors of diverse origin, i.e. the human macrophage galactose-type lectin, a plant lectin, Pisum sativum agglutinin, and the bacterial Gal-/Glc-binding protein from Escherichia coli, it became possible to simultaneously define their monosaccharide selectivity and identify the essential hydroxyls for interaction.

https://pubmed.ncbi.nlm.nih.gov/33258593