dc.creator | Fuente, Alex de la | es |
dc.creator | Mena Barragán, Teresa | es |
dc.creator | Farrar-Tobar, Ronald A. | es |
dc.creator | Verdaguer, Xavier | es |
dc.creator | García Fernández, José Manuel | es |
dc.creator | Ortiz Mellet, Carmen | es |
dc.creator | Riera, Antoni | es |
dc.date.accessioned | 2017-09-12T14:54:18Z | |
dc.date.available | 2017-09-12T14:54:18Z | |
dc.date.issued | 2015 | |
dc.identifier.citation | Fuente, A.d.l., Mena Barragán, T., Farrar-Tobar, R.A., Verdaguer, X., García Fernández, J.M., Ortiz Mellet, C. y Riera, A. (2015). Stereoselective synthesis of 2-acetamido-1,2-dideoxynojirimycin (DNJNAc) and ureido-DNJNAc derivatives as new hexosaminidase inhibitors. Organic and Biomolecular Chemistry, 13, 6500-6510. | |
dc.identifier.issn | 1477-0520 | es |
dc.identifier.uri | http://hdl.handle.net/11441/64349 | |
dc.description.abstract | 2-Acetamido-1,2-dideoxyiminosugars are selective and potent inhibitors of hexosaminidases and therefore show high therapeutic potential for the treatment of various diseases, including several lysosomal storage disorders. A stereoselective synthesis of 2-acetamido-1,2-dideoxynojirimycin (DNJNAc), the iminosugar analog of N-acetylglucosamine, with a high overall yield is here described. This novel procedure further allowed accessing ureido-DNJNAc conjugates through derivatization of the endocyclic amine on a key pivotal intermediate. Remarkably, some of the ureido-DNJNAc representatives behaved as potent and selective inhibitors of β-hexosaminidases, including the human enzyme, being the first examples of neutral sp2-iminosugar-type inhibitors reported for these enzymes. Moreover, the amphiphilic character of the new ureido-DNJNAc is expected to confer better drug-like properties. | es |
dc.description.sponsorship | Ministerio de Economía y Competitividad CTQ2011-23620, SAF2013-44021R y CTQ2010-15848 | es |
dc.description.sponsorship | Generalitat de Catalunya 2014SGR 234 | es |
dc.description.sponsorship | Junta de Andalucía FQM-1467 | es |
dc.format | application/pdf | es |
dc.language.iso | eng | es |
dc.publisher | Royal Society of Chemistry | es |
dc.relation.ispartof | Organic and Biomolecular Chemistry, 13, 6500-6510. | |
dc.rights | Attribution-NonCommercial-NoDerivatives 4.0 Internacional | * |
dc.rights.uri | http://creativecommons.org/licenses/by-nc-nd/4.0/ | * |
dc.title | Stereoselective synthesis of 2-acetamido-1,2-dideoxynojirimycin (DNJNAc) and ureido-DNJNAc derivatives as new hexosaminidase inhibitors | 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 | info:eu-repo/grantAgreement/MINECO/CTQ2011-23620 | es |
dc.relation.projectID | info:eu-repo/grantAgreement/MINECO/SAF2013-44021R | es |
dc.relation.projectID | info:eu-repo/grantAgreement/MINECO/CTQ2010-15848 | es |
dc.relation.projectID | 2014SGR 234 | es |
dc.relation.projectID | FQM-1467 | es |
dc.relation.publisherversion | http://dx.doi.org/ 10.1039/C5OB00507H | es |
dc.identifier.doi | 10.1039/C5OB00507H | es |
idus.format.extent | 11 p. | es |
dc.journaltitle | Organic and Biomolecular Chemistry | es |
dc.publication.volumen | 13 | es |
dc.publication.initialPage | 6500 | es |
dc.publication.endPage | 6510 | es |