title: Synthesis of 1,2-cis-homoiminosugars derived from GlcNAc and GalNAc exploiting a β-amino alcohol skeletal rearrangement.
abstract: The synthesis of 1,2-cis-homoiminosugars bearing an NHAc group at the C-2 position is described. The key step to prepare these α-D-GlcNAc and α-D-GalNAc mimics utilizes a β-amino alcohol skeletal rearrangement applied to an azepane precursor. This strategy also allows access to naturally occurring α-HGJ and α-HNJ. The α-D-GlcNAc-configured iminosugar was coupled to a glucoside acceptor to yield a novel pseudodisaccharide. Preliminary glycosidase inhibition evaluation indicates that the α-D-GalNAc-configured homoiminosugar is a potent and selective α-N-acetylgalactosaminidase inhibitor.
authors.affiliation: Glycochemistry Group of "Organic Synthesis" Team, Université de Poitiers , UMR-CNRS 7285 IC2MP, Bât. B28, 4 rue Michel Brunet, TSA 51106, 86073 Poitiers Cedex 9, France.
authors.forename: Yves
authors.initials: Y
authors.lastname: Blériot
authors.forename: Nicolas
authors.initials: N
authors.lastname: Auberger
authors.forename: Yerri
authors.initials: Y
authors.lastname: Jagadeesh
authors.forename: Charles
authors.initials: C
authors.lastname: Gauthier
authors.forename: Giuseppe
authors.initials: G
authors.lastname: Prencipe
authors.forename: Anh Tuan
authors.initials: AT
authors.lastname: Tran
authors.forename: Jérôme
authors.initials: J
authors.lastname: Marrot
authors.forename: Jérôme
authors.initials: J
authors.lastname: Désiré
authors.forename: Arisa
authors.initials: A
authors.lastname: Yamamoto
authors.forename: Atsushi
authors.initials: A
authors.lastname: Kato
authors.forename: Matthieu
authors.initials: M
authors.lastname: Sollogoub
mesh_terms: D000605:Amino Alcohols / Q000737:chemistry*; D000606:Amino Sugars / Q000737:chemistry*; D004791:Enzyme Inhibitors / Q000737:chemistry*; D005688:Galactosamine / Q000031:analogs & derivatives / Q000737:chemistry*; D005944:Glucosamine / Q000031:analogs & derivatives / Q000737:chemistry*; D015394:Molecular Structure; D048809:alpha-N-Acetylgalactosaminidase / Q000037:antagonists & inhibitors* / Q000737:chemistry*
chemical_list: D000605:Amino Alcohols; D000606:Amino Sugars; D004791:Enzyme Inhibitors; D005688:Galactosamine; D048809:alpha-N-Acetylgalactosaminidase; D005944:Glucosamine