Total synthesis and structural revision of TMG-chitotriomycin, a specific inhibitor of insect and fungal beta-N-acetylglucosaminidases

J Am Chem Soc. 2009 Sep 2;131(34):12076-7. doi: 10.1021/ja9055245.

Abstract

TMG-chitotriomycin, a potent and selective inhibitor of the beta-N-acetylglucosaminidases that possesses an unique N,N,N-trimethyl-d-glucosamine (TMG) residue, is revised to be the TMG-beta-(1-->4)-chitotriose instead of the originally proposed alpha-anomer via its total synthesis, for which a highly convergent approach was developed in which the sterically demanding (1-->4)-glycosidic linkages are efficiently constructed by the Au(I)-catalyzed glycosylation protocol with glycosyl o-hexynylbenzoates as donors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylglucosaminidase / antagonists & inhibitors*
  • Animals
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / pharmacology
  • Fungi / enzymology*
  • Humans
  • Insecta / enzymology*
  • Substrate Specificity
  • Sugar Alcohols / chemical synthesis*
  • Sugar Alcohols / chemistry*
  • Sugar Alcohols / pharmacology

Substances

  • Enzyme Inhibitors
  • Sugar Alcohols
  • TMG-chitotriomycin
  • Acetylglucosaminidase