Synthesis and NMR experiments of (4,5,6-13C)-deoxymannojirimycin. A new entry to 13C-labeled glycosidase inhibitors

Carbohydr Res. 2007 Sep 3;342(12-13):1805-12. doi: 10.1016/j.carres.2007.04.018. Epub 2007 Apr 29.

Abstract

The synthesis of (4,5,6-13C)-deoxymannojirimycin is described. The route employed is based on Sharpless asymmetric epoxidation of (1,2,3-13C)(E)-2,4-pentadien-1-ol and uses ring-closing metathesis as a key step. The labeled compound may be easily used for protein-binding experiments using NMR spectroscopic methods.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 1-Deoxynojirimycin / analogs & derivatives
  • 1-Deoxynojirimycin / chemical synthesis
  • 1-Deoxynojirimycin / chemistry*
  • 1-Deoxynojirimycin / pharmacology*
  • Carbon Isotopes
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology
  • Glycoside Hydrolases / antagonists & inhibitors*
  • Indicators and Reagents
  • Isotope Labeling
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Conformation

Substances

  • Carbon Isotopes
  • Enzyme Inhibitors
  • Indicators and Reagents
  • 1-Deoxynojirimycin
  • Glycoside Hydrolases