dc.creator | Cano, María Emilia | es |
dc.creator | Varela, Oscar | es |
dc.creator | García Moreno, M. Isabel | es |
dc.creator | García Fernández, José Manuel | es |
dc.creator | Kovensky, José | es |
dc.creator | Uhrig, María Laura | es |
dc.date.accessioned | 2022-12-21T14:40:02Z | |
dc.date.available | 2022-12-21T14:40:02Z | |
dc.date.issued | 2017 | |
dc.identifier.citation | Cano, M.E., Varela, O., García Moreno, M.I., García Fernández, J.M., Kovensky, J. y Uhrig, M.L. (2017). Synthesis of β-galactosylamides as Ligands of the Peanut Lectin. Insights into the Recognition Process. Carbohydrate Research, 443-444, 58-67. https://doi.org/10.1016/j.carres.2017.03.018. | |
dc.identifier.issn | 0008-6215 | es |
dc.identifier.issn | 1873-426X | es |
dc.identifier.uri | https://hdl.handle.net/11441/140734 | |
dc.description.abstract | The synthesis of mono and divalent β-galactosylamides linked to a hydroxylated chain having a C2 symmetry axis derived from L-tartaric anhydride is reported. Reference compounds devoid of hydroxyl groups in the linker were also prepared from β-galactosylamine and succinic anhydride. After functionalization with an alkynyl residue, the resulting building blocks were grafted onto different azide-equipped scaffolds through the copper catalyzed azide-alkyne cycloaddition. Thus, a family of structurally related mono and divalent β-N-galactopyranosylamides was obtained and fully characterized. The binding affinities of the ligands towards the model lectin PNA were measured by the enzyme-linked lectin assay (ELLA). The IC50 values were significantly higher than that of galactose but the presence of hydroxyl groups in the aglycone chain improved lectin recognition. Docking and molecular dynamics experiments were in accordance with the hypothesis that a hydroxyl group properly disposed in the linker could mimic the Glc O3 in the recognition process. On the other hand, divalent presentation of the ligands led to lectin affinity enhancements. | es |
dc.description.sponsorship | Consejo Nacional de Investigaciones Científicas y Técnicas UBACyT 2013–2016 GC, 20020120100101BA | es |
dc.description.sponsorship | Ministerio de Economía y Competitividad SAF2016-76083-R, CTQ2015-64425-C2-1-R | es |
dc.description.sponsorship | Junta de Andalucía FQM-1467 | es |
dc.format | application/pdf | es |
dc.format.extent | 11 p. | es |
dc.language.iso | eng | es |
dc.publisher | Elsevier | es |
dc.relation.ispartof | Carbohydrate Research, 443-444, 58-67. | |
dc.rights | Attribution-NonCommercial-NoDerivatives 4.0 Internacional | * |
dc.rights.uri | http://creativecommons.org/licenses/by-nc-nd/4.0/ | * |
dc.subject | Divalent ligands | es |
dc.subject | ELLA assay | es |
dc.subject | Molecular dynamics | es |
dc.subject | Peanut agglutinin | es |
dc.subject | β-galactosylamides | es |
dc.title | Synthesis of β-galactosylamides as Ligands of the Peanut Lectin. Insights into the Recognition Process | es |
dc.type | info:eu-repo/semantics/article | es |
dcterms.identifier | https://ror.org/03yxnpp24 | |
dc.type.version | info:eu-repo/semantics/acceptedVersion | es |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | es |
dc.contributor.affiliation | Universidad de Sevilla. Departamento de Química orgánica | es |
dc.relation.projectID | UBACyT 2013–2016 GC | es |
dc.relation.projectID | 20020120100101BA | es |
dc.relation.projectID | SAF2016-76083-R | es |
dc.relation.projectID | CTQ2015-64425-C2-1-R | es |
dc.relation.projectID | FQM-1467 | es |
dc.relation.publisherversion | https://doi.org/10.1016/j.carres.2017.03.018 | es |
dc.identifier.doi | 10.1016/j.carres.2017.03.018 | es |
dc.journaltitle | Carbohydrate Research | es |
dc.publication.volumen | 443-444 | es |
dc.publication.initialPage | 58 | es |
dc.publication.endPage | 67 | es |
dc.contributor.funder | Consejo Nacional de Investigaciones Científicas y Técnicas (CONICET). Argentina | es |
dc.contributor.funder | Centre national de la recherche scientifique (CNRS). France | es |
dc.contributor.funder | Ministerio de Economía y Competitividad (MINECO). España | es |
dc.contributor.funder | Junta de Andalucía | es |
dc.contributor.funder | European Commission (EC). Fondo Europeo de Desarrollo Regional (FEDER) | es |