期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 85, 期 24, 页码 16072-16081出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c01830
关键词
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资金
- Agencia Estatal de Investigacion (Spain) [CTQ2015-64597-C2-1-P, CTQ2015-64597-C2-2-P, RTI2018-094751-B-C21, RTI2018-094751-B-C22]
- Severo Ochoa Excellence Accreditation [SEV-2016-0644]
- European Research Council (RECGLYCANMR) [788143]
- CIBERES from the Spanish Institute of Health Carlos III
- Science Foundation Ireland [13/IA/1959]
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. F-19 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 F-19 NMR T-2 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.
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