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Fluorinated Carbohydrates as Lectin Ligands: Simultaneous Screening of a Monosaccharide Library and Chemical Mapping by 19F NMR Spectroscopy.
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.
Afiliación
  • Martínez JD; CIC bioGUNE, Basque Research Technology Alliance, BRTA, Bizkaia Technology Park, Building 800, 48160 Derio, Spain.
  • Manzano AI; Centro de Investigaciones Biológicas Margarita Salas, CSIC, Ramiro de Maeztu 9, 28040 Madrid, Spain.
  • Calviño E; Centro de Investigaciones Biológicas Margarita Salas, CSIC, Ramiro de Maeztu 9, 28040 Madrid, Spain.
  • Diego A; Centro de Investigaciones Biológicas Margarita Salas, CSIC, Ramiro de Maeztu 9, 28040 Madrid, Spain.
  • Rodriguez de Francisco B; Centro de Investigaciones Biológicas Margarita Salas, CSIC, Ramiro de Maeztu 9, 28040 Madrid, Spain.
  • Romanò C; Centre for Synthesis and Chemical Biology, University College Dublin, Belfield, Dublin 4, Ireland.
  • Oscarson S; Centre for Synthesis and Chemical Biology, University College Dublin, Belfield, Dublin 4, Ireland.
  • Millet O; CIC bioGUNE, Basque Research Technology Alliance, BRTA, Bizkaia Technology Park, Building 800, 48160 Derio, Spain.
  • Gabius HJ; Institute of Physiological Chemistry, Faculty of Veterinary Medicine, Ludwig-Maximilians-University Munich, 80539 Munich, Germany.
  • Jiménez-Barbero J; CIC bioGUNE, Basque Research Technology Alliance, BRTA, Bizkaia Technology Park, Building 800, 48160 Derio, Spain.
  • Cañada FJ; Ikerbasque, Basque Foundation for Science, 48009 Bilbao, Spain.
J Org Chem ; 85(24): 16072-16081, 2020 12 18.
Article en En | MEDLINE | ID: mdl-33258593
ABSTRACT
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.

Texto completo: 1 Banco de datos: MEDLINE Tipo de estudio: Diagnostic_studies / Screening_studies Idioma: En Año: 2020 Tipo del documento: Article

Texto completo: 1 Banco de datos: MEDLINE Tipo de estudio: Diagnostic_studies / Screening_studies Idioma: En Año: 2020 Tipo del documento: Article