title: Ferrier sulfamidoglycosylation of glycals catalyzed by nitrosonium tetrafluoroborate: towards new carbonic anhydrase glycoinhibitors.
abstract: Ferrier sulfamidoglycosylation of glycals catalyzed by nitrosonium tetrafluoroborate allowed the preparation of hydroxysulfamide glycosides in good yields with a good α stereoselectivity. A variety of mono-saccharide derivatives was synthesized using this new methodology leading to selective and powerful glycoinhibitors of the tumor associated carbonic anhydrases (CA, EC 4.2.1.1) isoforms CA IX and CA XII.
authors.affiliation: Institut des Biomolécules Max Mousseron (IBMM), UMR 5247 CNRS-UM1-UM2, Bâtiment de Recherche Max Mousseron, Ecole Nationale Supérieure de Chimie de Montpellier, 8 rue de l'Ecole Normale, 34296 Montpellier Cedex, France.
authors.forename: Joanna
authors.initials: J
authors.lastname: Ombouma
authors.affiliation: Laboratorio di Chimica Bioinorganica, Polo Scientifico, Università degli Studi di Firenze, Sesto Fiorentino, Florence, Italy.
authors.forename: Daniela
authors.initials: D
authors.lastname: Vullo
authors.affiliation: Neurofarba Department, Section of Pharmaceutical and Nutraceutical Sciences, Università degli Studi di Firenze, Sesto Fiorentino, Florence, Italy.
authors.forename: Claudiu T
authors.initials: CT
authors.lastname: Supuran
authors.affiliation: Institut des Biomolécules Max Mousseron (IBMM), UMR 5247 CNRS-UM1-UM2, Bâtiment de Recherche Max Mousseron, Ecole Nationale Supérieure de Chimie de Montpellier, 8 rue de l'Ecole Normale, 34296 Montpellier Cedex, France. Electronic address: jean-yves.winum@univ-montp2.fr.
authors.forename: Jean-Yves
authors.initials: JY
authors.lastname: Winum
mesh_terms: D000951:Antigens, Neoplasm / Q000737:chemistry / Q000378:metabolism; D001881:Borates / Q000737:chemistry*; D000071231:Carbonic Anhydrase IX; D002257:Carbonic Anhydrase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D002256:Carbonic Anhydrases / Q000737:chemistry* / Q000378:metabolism; D002384:Catalysis; D006031:Glycosylation; D007700:Kinetics; D009005:Monosaccharides / Q000737:chemistry; D009569:Nitric Oxide / Q000737:chemistry*; D011485:Protein Binding; D013237:Stereoisomerism; D013449:Sulfonamides / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism
chemical_list: D000951:Antigens, Neoplasm; D001881:Borates; D002257:Carbonic Anhydrase Inhibitors; D009005:Monosaccharides; D013449:Sulfonamides; C088437:nitrosonium tetrafluoroborate; D009569:Nitric Oxide; C089226:CA9 protein, human; D000071231:Carbonic Anhydrase IX; D002256:Carbonic Anhydrases; C477378:carbonic anhydrase XII
keywords: Carbonic anhydrase; Ferrier sulfamidoglycosylation; Glycals; Glycoinhibitor; Nitrosonium tetrafluoroborate