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Bioorg Med Chem. 2014 Nov 15;22(22):6353-9. doi: 10.1016/j.bmc.2014.09.053. Epub 2014 Oct 2.

Ferrier sulfamidoglycosylation of glycals catalyzed by nitrosonium tetrafluoroborate: towards new carbonic anhydrase glycoinhibitors.

Author information

1
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.
2
Laboratorio di Chimica Bioinorganica, Polo Scientifico, Università degli Studi di Firenze, Sesto Fiorentino, Florence, Italy.
3
Neurofarba Department, Section of Pharmaceutical and Nutraceutical Sciences, Università degli Studi di Firenze, Sesto Fiorentino, Florence, Italy.
4
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.

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.

KEYWORDS:

Carbonic anhydrase; Ferrier sulfamidoglycosylation; Glycals; Glycoinhibitor; Nitrosonium tetrafluoroborate

PMID:
25438758
DOI:
10.1016/j.bmc.2014.09.053
[Indexed for MEDLINE]

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