Generalized anomeric effect in gem-diamines: stereoselective synthesis of alpha-N-linked disaccharide mimics

Org Lett. 2009 Aug 6;11(15):3306-9. doi: 10.1021/ol901125n.

Abstract

The orbital (negative hyperconjugation) contribution to the generalized anomeric effect is highly increased in bicyclic gem-diamines with a pseudoamide-type endocyclic nitrogen atom, which has been exploited for the stereoselective synthesis of configurationally stable alpha-N-linked azadisaccharide heteroanalogues of the natural disaccharides maltose and isomaltose as aglycon-sensitive inhibitors of isomaltase.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Diamines / chemistry*
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology
  • Glucosamine / analogs & derivatives*
  • Glucosamine / chemical synthesis
  • Glucosamine / chemistry
  • Isomaltose / chemical synthesis*
  • Isomaltose / chemistry
  • Isomaltose / pharmacology
  • Maltose / chemical synthesis*
  • Maltose / chemistry
  • Maltose / pharmacology
  • Molecular Mimicry*
  • Oligo-1,6-Glucosidase / antagonists & inhibitors*
  • Stereoisomerism

Substances

  • Diamines
  • Enzyme Inhibitors
  • Isomaltose
  • Maltose
  • glucopyranosylamine
  • Oligo-1,6-Glucosidase
  • Glucosamine