4.7 Article

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

Journal

BIOORGANIC & MEDICINAL CHEMISTRY
Volume 22, Issue 22, Pages 6353-6359

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2014.09.053

Keywords

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

Funding

  1. Gabonese Ministry of Research
  2. CNRS/CNR (CoopIn-tEER Program) [131999]

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Ferrier sulfamidoglycosylation of glycals catalyzed by nitrosonium tetrafluoroborate allowed the preparation of hydroxysulfamide glycosides in good yields with a good a stereoselectivity. A variety of monosaccharide 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. (C) 2014 Elsevier Ltd. All rights reserved.

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