dc.creator | Lumbroso, Alexandre | es |
dc.creator | Berthonneau, Clément | es |
dc.creator | Beaudet, Isabelle | es |
dc.creator | Quintard, Jean Paul | es |
dc.creator | Planchat, Aurélien | es |
dc.creator | García Moreno, M. Isabel | es |
dc.creator | Ortiz Mellet, Carmen | es |
dc.creator | Le Grognec, Erwan | es |
dc.date.accessioned | 2023-01-17T08:10:40Z | |
dc.date.available | 2023-01-17T08:10:40Z | |
dc.date.issued | 2021 | |
dc.identifier.citation | Lumbroso, A., Berthonneau, C., Beaudet, I., Quintard, J.P., Planchat, A., García Moreno, M.I.,...,Le Grognec, E. (2021). A versatile stereocontrolled synthesis of 2-deoxyiminosugarC-glycosides and their evaluation as glycosidase inhibitors. Organic and Biomolecular Chemistry, 19 (5), 1083-1099. https://doi.org/10.1039/D0OB02249G. | |
dc.identifier.issn | 1477-0520 | es |
dc.identifier.issn | 1477-0539 | es |
dc.identifier.uri | https://hdl.handle.net/11441/141423 | |
dc.description.abstract | A highly enantioselective synthesis of (R,S) or (S,S)-2,6-disubstituted dehydropiperidines has been previously achieved through Sn/Li transmetalation of the corresponding stannylated dehydropiperidines or of
their precursors. Herein, we successively consider their Upjohn’s syn dihydroxylation and their anti-dihydroxylation via an epoxidation reaction followed by epoxide opening reaction. The stereochemical course
of these reactions was first reported including the use of appropriate protecting groups before considering the conversion of the obtained compounds into NH or NMe iminosugar hydrochlorides. A primary
evaluation of the designed iminosugar C-glycosides as glycosidase inhibitors suggests candidates for the
selective inhibition of α-galactosidase, amyloglycosidase and naringinase. Beyond the reported results,
the method constitutes a highly modulable route for the synthesis of well stereodefined iminosugar
C-glycosides, an advantage which might be used for the design of iminosugars to enhance their biological properties. | es |
dc.description.sponsorship | Institut de Chimie des Substances Naturelles de Francia-ICSN, UPR CNRS 2301 | es |
dc.description.sponsorship | Ministère de l'Enseignement Supérieur, de la Recherche et de l’Innovation (MESRI) de Francia-UMR CNRS 6521 y UMR CNRS 6230 | es |
dc.description.sponsorship | Ministerio de Ciencia e Innovación y Agencia Estatal de Investigación de España y fondos FEDER de la Unión Europea (MCI, AEI, FEDER, UE)-PID2019-105858RB-I00 | es |
dc.format | application/pdf | es |
dc.format.extent | 17 p. | es |
dc.language.iso | eng | es |
dc.publisher | Royal Society of Chemistry | es |
dc.relation.ispartof | Organic and Biomolecular Chemistry, 19 (5), 1083-1099. | |
dc.rights | Attribution-NonCommercial-NoDerivatives 4.0 Internacional | |
dc.rights.uri | http://creativecommons.org/licenses/by-nc-nd/4.0/ | |
dc.title | A versatile stereocontrolled synthesis of 2-deoxyiminosugarC-glycosides and their evaluation as glycosidase 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.rights.accessRights | info:eu-repo/semantics/openAccess | |
dc.contributor.affiliation | Universidad de Sevilla. Departamento de Química orgánica | es |
dc.relation.projectID | ICSN, UPR CNRS 2301 | es |
dc.relation.projectID | UMR CNRS 6521 | es |
dc.relation.projectID | UMR CNRS 6230 | es |
dc.relation.projectID | PID2019-105858RB-I00 | es |
dc.relation.publisherversion | https://doi.org/10.1039/D0OB02249G | es |
dc.identifier.doi | 10.1039/D0OB02249G | es |
dc.journaltitle | Organic and Biomolecular Chemistry | es |
dc.publication.volumen | 19 | es |
dc.publication.issue | 5 | es |
dc.publication.initialPage | 1083 | es |
dc.publication.endPage | 1099 | es |
dc.contributor.funder | Institut de Chimie des Substances Naturelles (ICSN). France | es |
dc.contributor.funder | Ministère de l'Enseignement Supérieur, de la Recherche et de l’Innovation (MESRI). France | es |
dc.contributor.funder | Université de Rennes. France | es |
dc.contributor.funder | Ministerio de Ciencia e Innovación (MICIN). España | es |
dc.contributor.funder | Agencia Estatal de Investigación. España | es |
dc.contributor.funder | European Commission (EC). Fondo Europeo de Desarrollo Regional (FEDER) | es |