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Stereoselective synthesis of 2-acetamido-1,2-dideoxynojirimycin (DNJNAc) and ureido-DNJNAc derivatives as new hexosaminidase inhibitors
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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.
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FUENTE CEBRIÁN, Àlex de la, MENA-BARRAGÁN, Teresa, FARRAR-TOBAR, Ronald a., VERDAGUER I ESPAULELLA, Xavier, GARCÍA-FERNÁNDEZ, J. m., ORTIZ MELLET, Carmen, RIERA I ESCALÉ, Antoni. Stereoselective synthesis of 2-acetamido-1,2-dideoxynojirimycin (DNJNAc) and ureido-DNJNAc derivatives as new hexosaminidase inhibitors. _Organic & Biomolecular Chemistry_. 2015. Vol. 13, núm. 6500-6510. [consulta: 21 de gener de 2026]. ISSN: 1477-0520. [Disponible a: https://hdl.handle.net/2445/101685]