An efficient synthesis of methyl tetra-O-hexyl gentiooctaoside, an octaosyl analogue of ANP receptor antagonist HS-142-1

Bioorg Med Chem. 1996 Dec;4(12):2035-42. doi: 10.1016/s0968-0896(96)00214-3.

Abstract

Methyl 0-(3-0-hexyl-beta-D-glucopyranosyl)-(1->6)-[0-(beta-D-glucopyranosyl)-(1 ->6)-0-(3-0-hexyl-beta-D-glucopyranosyl)-(1->6)3-beta-D- glucopyranoside, a 3-0 hexyl analogue of the octaosyl component of fungal lipooligosaccharide HS-142-1, was stereo- and regioselectively synthesized as a potent antagonist for the tetrameric atrial natriuretic peptide (ANP) receptors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Atrial Natriuretic Factor / antagonists & inhibitors
  • Atrial Natriuretic Factor / pharmacology
  • Binding, Competitive
  • Carbohydrate Sequence
  • Cell Membrane / drug effects
  • Cell Membrane / metabolism
  • Glycosylation
  • Kidney / drug effects
  • Kidney / metabolism
  • Molecular Sequence Data
  • Oligosaccharides / chemical synthesis*
  • Oligosaccharides / chemistry
  • Oligosaccharides / pharmacology
  • Polysaccharides / chemistry*
  • Polysaccharides / pharmacology
  • Rats

Substances

  • HS 142-1
  • Oligosaccharides
  • Polysaccharides
  • methyl tetra-O-hexyl gentiooctaoside
  • Atrial Natriuretic Factor