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

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

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antigens, Neoplasm / chemistry
  • Antigens, Neoplasm / metabolism
  • Borates / chemistry*
  • Carbonic Anhydrase IX
  • Carbonic Anhydrase Inhibitors / chemical synthesis
  • Carbonic Anhydrase Inhibitors / chemistry*
  • Carbonic Anhydrase Inhibitors / metabolism
  • Carbonic Anhydrases / chemistry*
  • Carbonic Anhydrases / metabolism
  • Catalysis
  • Glycosylation
  • Kinetics
  • Monosaccharides / chemistry
  • Nitric Oxide / chemistry*
  • Protein Binding
  • Stereoisomerism
  • Sulfonamides / chemical synthesis
  • Sulfonamides / chemistry*
  • Sulfonamides / metabolism

Substances

  • Antigens, Neoplasm
  • Borates
  • Carbonic Anhydrase Inhibitors
  • Monosaccharides
  • Sulfonamides
  • nitrosonium tetrafluoroborate
  • Nitric Oxide
  • CA9 protein, human
  • Carbonic Anhydrase IX
  • Carbonic Anhydrases
  • carbonic anhydrase XII