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.
Copyright © 2014 Elsevier Ltd. All rights reserved.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Antigens, Neoplasm / chemistry
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Antigens, Neoplasm / metabolism
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Borates / chemistry*
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Carbonic Anhydrase IX
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Carbonic Anhydrase Inhibitors / chemical synthesis
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Carbonic Anhydrase Inhibitors / chemistry*
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Carbonic Anhydrase Inhibitors / metabolism
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Carbonic Anhydrases / chemistry*
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Carbonic Anhydrases / metabolism
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Catalysis
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Glycosylation
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Kinetics
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Monosaccharides / chemistry
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Nitric Oxide / chemistry*
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Protein Binding
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Stereoisomerism
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Sulfonamides / chemical synthesis
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Sulfonamides / chemistry*
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Sulfonamides / metabolism
Substances
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Antigens, Neoplasm
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Borates
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Carbonic Anhydrase Inhibitors
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Monosaccharides
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Sulfonamides
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nitrosonium tetrafluoroborate
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Nitric Oxide
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CA9 protein, human
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Carbonic Anhydrase IX
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Carbonic Anhydrases
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carbonic anhydrase XII