Artículo
A versatile stereocontrolled synthesis of 2-deoxyiminosugarC-glycosides and their evaluation as glycosidase inhibitors
Autor/es | Lumbroso, Alexandre
Berthonneau, Clément Beaudet, Isabelle Quintard, Jean Paul Planchat, Aurélien García Moreno, M. Isabel Ortiz Mellet, Carmen Le Grognec, Erwan |
Departamento | Universidad de Sevilla. Departamento de Química orgánica |
Fecha de publicación | 2021 |
Fecha de depósito | 2023-01-17 |
Publicado en |
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Resumen | 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. ... 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. |
Agencias financiadoras | Institut de Chimie des Substances Naturelles (ICSN). France Ministère de l'Enseignement Supérieur, de la Recherche et de l’Innovation (MESRI). France Université de Rennes. France Ministerio de Ciencia e Innovación (MICIN). España Agencia Estatal de Investigación. España European Commission (EC). Fondo Europeo de Desarrollo Regional (FEDER) |
Identificador del proyecto | ICSN, UPR CNRS 2301
UMR CNRS 6521 UMR CNRS 6230 PID2019-105858RB-I00 |
Cita | 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. |
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