| Autor: |
Martínez, J. Daniel, Manzano, Ana I., Calviño, Eva, Diego, Ana de, Rodriguez de Francisco, Borja, Romanò, Cecilia, Oscarson, Stefan, Millet, Oscar, Gabius, Hans-Joachim, Jiménez-Barbero, Jesús, Cañada, Francisco J. |
| Zdroj: |
The Journal of Organic Chemistry; December 2020, Vol. 85 Issue: 24 p16072-16081, 10p |
| Abstrakt: |
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 T2filtering-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 sativumagglutinin, 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. |
| Databáze: |
Supplemental Index |
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