Stereoselective Synthesis of 2‑Acetamido-1,2-dideoxyallonojirimycin (DAJNAc), a New Potent Hexosaminidase Inhibitor

Stereoselective Synthesis of 2‑Acetamido-1,2-dideoxyallonojirimycin (DAJNAc), a New Potent Hexosaminidase Inhibitor

A practical synthesis of the previously unreported N-acetyl-d-allosamine glycomimetic DAJNAc is described. The reaction sequence involves Pd-catalyzed allylic substitution by phthalimide in an azaheterobicyclic scaffold as the key step. The new iminosugar resulted in being a stronger β-N-acetylgluco...

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Veröffentlicht in:Organic letters 2013-07, Vol.15 (14), p.3638-3641
Hauptverfasser: de la Fuente, Alex, Martin, Ruben, Mena-Barragán, Teresa, Verdaguer, Xavier, García Fernández, José M, Ortiz Mellet, Carmen, Riera, Antoni
Format: Artikel
Sprache:eng
Schlagworte:
1-Deoxynojirimycin - analogs & derivatives
1-Deoxynojirimycin - chemical synthesis
1-Deoxynojirimycin - chemistry
beta-N-Acetylhexosaminidases - chemical synthesis
beta-N-Acetylhexosaminidases - chemistry
Female
Hexosaminidases - analysis
Hexosaminidases - chemistry
Humans
Pregnancy
Stereoisomerism
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Zusammenfassung:A practical synthesis of the previously unreported N-acetyl-d-allosamine glycomimetic DAJNAc is described. The reaction sequence involves Pd-catalyzed allylic substitution by phthalimide in an azaheterobicyclic scaffold as the key step. The new iminosugar resulted in being a stronger β-N-acetylglucosaminidase (human placenta) competitive inhibitor than the d-gluco (DNJNAc) and d-galacto (DGJNAc) stereoisomers.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol401517x