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Stereoselective synthesis of 2-acetamido-1,2-dideoxynojirimycin (DNJNAc) and ureido-DNJNAc derivatives as new hexosaminidase inhibitors

AutorDe la Fuente, A.; Mena-Barragán, Teresa; Farrar-Tobar, Ronald A.; Verdaguer, Xavier; García-Fernández, José Manuel; Ortiz-Mellet, Carmen; Riera, Antoni
Fecha de publicación2015
EditorRoyal Society of Chemistry (Great Britain)
CitaciónOrganic and Biomolecular Chemistry, 13:6500-6510 (2015)
Resumen2-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.
Versión del editorhttp://dx.doi.org/ 10.1039/C5OB00507H
URIhttp://hdl.handle.net/10261/116975
DOI10.1039/C5OB00507H
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