α-L-Arabinofuranosylated pyrrolidines as arabinanase inhibitors

Chem Commun (Camb). 2011 Sep 14;47(34):9684-6. doi: 10.1039/c1cc13675e. Epub 2011 Jul 20.

Abstract

As part of continued efforts to understand the mechanisms of 1,5-α-l-arabinanases better, some arabinan-like iminosugar oligosaccharides were synthesized. An iminosugar analogue of arabinobiose was found to be a good inhibitor of the arabinanase Arb93A from Fusarium graminearum. Structures were determined for complexes of this inhibitor with wild-type Arb93A and a catalytically inactive mutant.

MeSH terms

  • Arabinose / analogs & derivatives*
  • Arabinose / chemistry
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / pharmacology*
  • Glycoside Hydrolases / antagonists & inhibitors*
  • Glycoside Hydrolases / chemistry
  • Models, Molecular
  • Protein Conformation
  • Pyrrolidines / chemical synthesis
  • Pyrrolidines / chemistry*
  • Pyrrolidines / pharmacology*

Substances

  • Enzyme Inhibitors
  • Pyrrolidines
  • arabinofuranose
  • Arabinose
  • Glycoside Hydrolases
  • exo-alpha-L-arabinanase
  • pyrrolidine