2-Acetamino-1,2-dideoxynojirimycin—lysine hybrids as hexosaminidase inhibitors

2-Acetamino-1,2-dideoxynojirimycin—lysine hybrids as hexosaminidase inhibitors

Cyclisation by double reductive amination of 2-acetamino-2-deoxy- d- xylo-hexos-5-ulose with N-2 protected l-lysine derivatives provided 2-acetamino-1,2-dideoxynojirimycin derivatives without any observable epimer formation at C-5. Modifications on the lysine moiety gave access to lipophilic derivat...

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Veröffentlicht in:Tetrahedron: asymmetry 2009-05, Vol.20 (6), p.832-835
Hauptverfasser: Steiner, Andreas J., Schitter, Georg, Stütz, Arnold E., Wrodnigg, Tanja M., Tarling, Chris A., Withers, Stephen G., Mahuran, Don J., Tropak, Michael B.
Format: Artikel
Sprache:eng
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Zusammenfassung:Cyclisation by double reductive amination of 2-acetamino-2-deoxy- d- xylo-hexos-5-ulose with N-2 protected l-lysine derivatives provided 2-acetamino-1,2-dideoxynojirimycin derivatives without any observable epimer formation at C-5. Modifications on the lysine moiety gave access to lipophilic derivatives that exhibited improved hexosaminidase inhibitory activities.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2009.02.015