title: Synthesis of 1,2-trans-2-acetamido-2-deoxyhomoiminosugars.
abstract: The first synthesis of 1,2-trans-homoiminosugars devised as mimics of β-D-GlcNAc and α-D-ManNAc is described. Key steps include a regioselective azidolysis of a cyclic sulfite and a β-amino alcohol skeletal rearrangement applied to a polyhydroxylated azepane. The β-D-GlcNAc derivative has been coupled to serine to deliver an iminosugar C-amino acid. The two homoiminosugars demonstrate moderate glycosidase inhibition.
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: Anh Tuan
authors.initials: AT
authors.lastname: Tran
authors.forename: Giuseppe
authors.initials: G
authors.lastname: Prencipe
authors.forename: Yerri
authors.initials: Y
authors.lastname: Jagadeesh
authors.forename: Nicolas
authors.initials: N
authors.lastname: Auberger
authors.forename: Sha
authors.initials: S
authors.lastname: Zhu
authors.forename: Charles
authors.initials: C
authors.lastname: Gauthier
authors.forename: Yongmin
authors.initials: Y
authors.lastname: Zhang
authors.forename: Jérôme
authors.initials: J
authors.lastname: Désiré
authors.forename: Isao
authors.initials: I
authors.lastname: Adachi
authors.forename: Atsushi
authors.initials: A
authors.lastname: Kato
authors.forename: Matthieu
authors.initials: M
authors.lastname: Sollogoub
mesh_terms: D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D004791:Enzyme Inhibitors / Q000737:chemistry*; D005688:Galactosamine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D005944:Glucosamine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors* / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
chemical_list: D000605:Amino Alcohols; D004791:Enzyme Inhibitors; D006571:Heterocyclic Compounds; D005688:Galactosamine; D006026:Glycoside Hydrolases; D005944:Glucosamine