Academic Journal
Stereoselective synthesis of 2-acetamido-1,2-dideoxynojirimycin (DNJNAc) and ureido-DNJNAc derivatives as new hexosaminidase inhibitors
| العنوان: | Stereoselective synthesis of 2-acetamido-1,2-dideoxynojirimycin (DNJNAc) and ureido-DNJNAc derivatives as new hexosaminidase inhibitors |
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| المؤلفون: | De la Fuente, A., Mena-Barragán, Teresa, Farrar-Tobar, Ronald A., Verdaguer, Xavier, García-Fernández, José Manuel, Ortiz-Mellet, Carmen, Riera, Antoni |
| بيانات النشر: | Royal Society of Chemistry (UK) |
| سنة النشر: | 2015 |
| المجموعة: | Digital.CSIC (Consejo Superior de Investigaciones Científicas / Spanish National Research Council) |
| الوصف: | 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. ; Peer reviewed |
| نوع الوثيقة: | article in journal/newspaper |
| اللغة: | English |
| Relation: | Postprint; http://dx.doi.org/ 10.1039/C5OB00507H; Sí; Organic and Biomolecular Chemistry, 13:6500-6510 (2015); http://hdl.handle.net/10261/116975 |
| DOI: | 10.1039/C5OB00507H |
| الاتاحة: | http://hdl.handle.net/10261/116975 https://doi.org/10.1039/C5OB00507H |
| Rights: | open |
| رقم الانضمام: | edsbas.30D540D0 |
| قاعدة البيانات: | BASE |
| DOI: | 10.1039/C5OB00507H |
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