dc.contributor.author | Martínez, José Daniel | |
dc.contributor.author | Manzano, Ana I. | |
dc.contributor.author | Calviño, Eva | |
dc.contributor.author | De Diego, Ana | |
dc.contributor.author | Rodríguez de Francisco, Borja | |
dc.contributor.author | Romanó, Cecilia | |
dc.contributor.author | Oscarson, Stefan | |
dc.contributor.author | Millet Aguilar-Galindo, Oscar | |
dc.contributor.author | Gabius, Hans Joachim | |
dc.contributor.author | Jiménez Barbero, Jesús | |
dc.contributor.author | Cañada Vicinay, Francisco Javier | |
dc.date.accessioned | 2021-04-09T11:48:29Z | |
dc.date.available | 2021-04-09T11:48:29Z | |
dc.date.issued | 2020-12-18 | |
dc.identifier.citation | Journal Of Organic Chemistry 85(24) : 16072-16081 (2020) | es_ES |
dc.identifier.issn | 0022-3263 | |
dc.identifier.issn | 1520-6904 | |
dc.identifier.uri | http://hdl.handle.net/10810/50872 | |
dc.description.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. 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 | es_ES |
dc.description.sponsorship | Agencia Estatal de Investigacion (Spain) Grants CTQ2015-64597-C2-1-P and 2-P, RTI2018-094751-B-C21 and C22, Severo Ochoa Excellence Accreditation (SEV-2016-0644) European Research Council (RECGLYCANMR, Advanced Grant No. 788143), and CIBERES, an initiative from the Spanish Institute of Health Carlos III. Science Foundation Ireland, SFI Award 13/IA/1959 | es_ES |
dc.language.iso | eng | es_ES |
dc.publisher | American Chemical Society | es_ES |
dc.relation | info:eu-repo/grantAgreement/MICINN/CTQ2015-64597-C2-1-P | es_ES |
dc.relation | info:eu-repo/grantAgreement/MICINN/CTQ2015-64597-C2-2-P | es_ES |
dc.relation | info:eu-repo/grantAgreement/MICINN/RTI2018-094751-B-C21 | es_ES |
dc.relation | info:eu-repo/grantAgreement/MICINN/RTI2018-094751-B-C22 | es_ES |
dc.relation | info:eu-repo/grantAgreement/MICINN/SEV-2016-0644 | es_ES |
dc.relation | info:eu-repo/grantAgreement/EC/H2020/788143 | es_ES |
dc.rights | info:eu-repo/semantics/openAccess | es_ES |
dc.rights.uri | http://creativecommons.org/licenses/by-nc-nd/3.0/es/ | * |
dc.subject | pisum-sativum lectin | es_ES |
dc.subject | molecular recognition | es_ES |
dc.subject | binding-protein | es_ES |
dc.subject | concanavalin-A | es_ES |
dc.subject | specificity | es_ES |
dc.subject | galactose | es_ES |
dc.subject | mechanism | es_ES |
dc.subject | relaxation | es_ES |
dc.subject | transport | es_ES |
dc.subject | receptor | es_ES |
dc.title | Fluorinated Carbohydrates as Lectin Ligands: Simultaneous Screening of a Monosaccharide Library and Chemical Mapping by F-19 NMR Spectroscopy | es_ES |
dc.type | info:eu-repo/semantics/article | es_ES |
dc.rights.holder | This is an open access article published under a Creative Commons Non Commercial No Derivative Works (CC-BY-NC-ND) Attribution License | es_ES |
dc.rights.holder | Atribución-NoComercial-SinDerivadas 3.0 España | * |
dc.relation.publisherversion | https://pubs.acs.org/doi/10.1021/acs.joc.0c01830 | es_ES |
dc.identifier.doi | 10.1021/acs.joc.0c01830 | |
dc.contributor.funder | European Commission | |
dc.departamentoes | Química orgánica II | es_ES |
dc.departamentoeu | Kimika organikoa II | es_ES |