1 research outputs found
Synthesis of 1,2-<i>cis</i>-Homoiminosugars Derived from GlcNAc and GalNAc Exploiting a Ī²āAmino Alcohol Skeletal Rearrangement
The synthesis of 1,2-<i>cis</i>-homoiminosugars bearing
an NHAc group at the C-2 position is described. The key step to prepare
these Ī±-d-GlcNAc and Ī±-d-GalNAc mimics
utilizes a Ī²-amino alcohol skeletal rearrangement applied to
an azepane precursor. This strategy also allows access to naturally
occurring Ī±-HGJ and Ī±-HNJ. The Ī±-d-GlcNAc-configured
iminosugar was coupled to a glucoside acceptor to yield a novel pseudodisaccharide.
Preliminary glycosidase inhibition evaluation indicates that the Ī±-d-GalNAc-configured homoiminosugar is a potent and selective
Ī±-<i>N</i>-acetylgalactosaminidase inhibitor