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Ferrier sulfamidoglycosylation of glycals catalyzed by nitrosonium tetrafluoroborate: Towards new carbonic anhydrase glycoinhibitors
Journal article   Peer reviewed

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

Joanna Ombouma, Daniela Vullo, Claudiu Supuran and Jean-Yves Winum
Bioorganic and Medicinal Chemistry, Vol.22(22), pp.6353-6359
11/2014
PMID: 25438758

Abstract

Carbonic anhydrase Ferrier sulfamidoglycosylation Glycals Glycoinhibitor Nitrosonium tetrafluoroborate Antigens, Neoplasm Borates Protein Binding Stereoisomerism Sulfonamides Carbonic Anhydrase IX Carbonic Anhydrase Inhibitors Carbonic Anhydrases Catalysis Glycosylation Kinetics Monosaccharides Nitric Oxide
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.
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