title: Synthesis of pyrrolidine-based analogues of 2-acetamidosugars as N-acetyl-D-glucosaminidase inhibitors.
abstract: A ring-contraction strategy applied to β-azido,γ-hydroxyazepanes yielded after functional group manipulation new tetrahydroxylated pyrrolidines displaying an acetamido moiety, one of these iminosugars demonstrating low micromolar inhibition on N-acetylglucosaminidases.
authors.affiliation: Sorbonne Universités, UPMC Univ Paris 06, Institut Universitaire de France, UMR-CNRS 8232, IPCM, F-75005 Paris, France.
authors.forename: Anh Tuan
authors.initials: AT
authors.lastname: Tran
authors.affiliation: Sorbonne Universités, UPMC Univ Paris 06, Institut Universitaire de France, UMR-CNRS 8232, IPCM, F-75005 Paris, France.
authors.forename: Bo
authors.initials: B
authors.lastname: Luo
authors.affiliation: Glycochemistry Group of "Organic Synthesis" Team, Université de Poitiers, UMR-CNRS 7285 IC2MP, 4 rue Michel Brunet, 86073 Poitiers Cedex 9, France.
authors.forename: Yerri
authors.initials: Y
authors.lastname: Jagadeesh
authors.affiliation: Glycochemistry Group of "Organic Synthesis" Team, Université de Poitiers, UMR-CNRS 7285 IC2MP, 4 rue Michel Brunet, 86073 Poitiers Cedex 9, France.
authors.forename: Nicolas
authors.initials: N
authors.lastname: Auberger
authors.affiliation: Glycochemistry Group of "Organic Synthesis" Team, Université de Poitiers, UMR-CNRS 7285 IC2MP, 4 rue Michel Brunet, 86073 Poitiers Cedex 9, France.
authors.forename: Jérôme
authors.initials: J
authors.lastname: Désiré
authors.affiliation: Department of Hospital Pharmacy, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan.
authors.forename: Shinpei
authors.initials: S
authors.lastname: Nakagawa
authors.affiliation: Department of Hospital Pharmacy, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan.
authors.forename: Atsushi
authors.initials: A
authors.lastname: Kato
authors.affiliation: Sorbonne Universités, UPMC Univ Paris 06, Institut Universitaire de France, UMR-CNRS 8232, IPCM, F-75005 Paris, France.
authors.forename: Yongmin
authors.initials: Y
authors.lastname: Zhang
authors.affiliation: Glycochemistry Group of "Organic Synthesis" Team, Université de Poitiers, UMR-CNRS 7285 IC2MP, 4 rue Michel Brunet, 86073 Poitiers Cedex 9, France. Electronic address: yves.bleriot@univ-poitiers.fr.
authors.forename: Yves
authors.initials: Y
authors.lastname: Blériot
authors.affiliation: Sorbonne Universités, UPMC Univ Paris 06, Institut Universitaire de France, UMR-CNRS 8232, IPCM, F-75005 Paris, France. Electronic address: matthieu.sollogoub@upmc.fr.
authors.forename: Matthieu
authors.initials: M
authors.lastname: Sollogoub
mesh_terms: D004789:Enzyme Activation / Q000187:drug effects; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry*; D006596:Hexosaminidases / Q000037:antagonists & inhibitors*; D050111:Imino Sugars / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D011759:Pyrrolidines
chemical_list: D004791:Enzyme Inhibitors; D050111:Imino Sugars; D011759:Pyrrolidines; D006596:Hexosaminidases; C032519:pyrrolidine
keywords: Glycosidase inhibitors; Iminosugars; Pyrrolidines; Ring-contraction