Chemoenzymatic syntheses of (-)-1-deoxymannojirimycin (DMJ) and its naturally occurring 6-O-alpha-L-rhamnopyranosyl glycoside

Org Biomol Chem. 2003 Jun 21;1(12):2035-7. doi: 10.1039/b304063a.

Abstract

The naturally occurring sugar mimetic alkaloids 1-deoxymannojirimycin (DMJ, 1) and 6-O-alpha-L-rhamnopyranosyl-DMJ (2) have each been prepared in a completely stereoselective manner from the cis-1,2-dihydrocatechol 3, itself obtained in enantiomerically pure form by microbial oxidation of chlorobenzene.

MeSH terms

  • 1-Deoxynojirimycin / chemical synthesis*
  • 1-Deoxynojirimycin / pharmacology
  • Animals
  • Catechols / chemistry
  • Cattle
  • Chlorobenzenes / chemistry
  • Chlorobenzenes / metabolism
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / pharmacology
  • Glycoside Hydrolases / antagonists & inhibitors
  • Glycosides / chemical synthesis*
  • Glycosides / chemistry
  • Glycosides / pharmacology
  • Humans
  • Oxidation-Reduction
  • Rats
  • Rhamnose / analogs & derivatives
  • Rhamnose / chemical synthesis
  • Rhamnose / pharmacology
  • Stereoisomerism

Substances

  • Catechols
  • Chlorobenzenes
  • Enzyme Inhibitors
  • Glycosides
  • 1-Deoxynojirimycin
  • Glycoside Hydrolases
  • Rhamnose