1-Deoxygalactonojirimycin-lysine hybrids as potent D-galactosidase inhibitors

Bioorg Med Chem. 2008 Dec 15;16(24):10216-20. doi: 10.1016/j.bmc.2008.10.054. Epub 2008 Oct 26.

Abstract

Cyclization by double reductive amination of L-arabino-hexos-5-ulose with suitably protected D- as well as L-lysine derivatives provided 1-deoxygalactonojirimycin lysine hybrids without any observable epimer formation at C-5. Modifications on the lysine moiety by acylation gave access to lipophilic derivatives which exhibited excellent D-galactosidase inhibitory activities.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 1-Deoxynojirimycin / chemistry*
  • Acylation
  • Chimera
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / metabolism
  • Enzyme Inhibitors / pharmacology
  • Galactosidases / antagonists & inhibitors*
  • Galactosidases / metabolism
  • Kinetics
  • Lysine / chemistry*

Substances

  • Enzyme Inhibitors
  • 1-Deoxynojirimycin
  • Galactosidases
  • Lysine