Syntheses of new model compounds related to an antigenic epitope from Bupleurum falcatum L. and their distributions in various ganglioside-phospholipid monolayers

Chem Pharm Bull (Tokyo). 2006 Sep;54(9):1281-4. doi: 10.1248/cpb.54.1281.

Abstract

6-N-[2-(Tetradecyl)hexadecanamido]hexyl beta-D-glucopyranosyluronic acid-(1-->6)-beta-D-galactopyranosyl-(1-->6)-beta-D-galactopyranoside (1) and its clustering compound (2) carrying a tetravalent sugar unit, which are new model compounds related to a major antigenic epitope from antiulcer pectic polysaccharide of Bupleurum falcatum L., were synthesized and the distributions of 1 and 2 in mixed ganglioside (GM1, GD1a or GT1b)/phospholipid (DPPC) monolayers were observed using atomic force microscopy (AFM). AFM images showed that 1 was distributed in the GM1, GD1a and GT1b region of the mixed monolayers, in which 1 was miscible with GD1a. Specific distribution of 1 was observed in the mixed GM1/DPPC monolayer. Compound 2 was miscible with GM1, while 2 formed associations with GD1a and GT1b in the mixed monolayers. The distribution mode of 1 and 2 was different among the mixed ganglioside/DPPC monolayers.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bupleurum / chemistry*
  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Epitopes / chemistry*
  • Epitopes / immunology
  • Gangliosides / chemistry*
  • Membranes, Artificial*
  • Microscopy, Atomic Force
  • Molecular Sequence Data
  • Particle Size
  • Pectins / chemistry
  • Phospholipids / chemical synthesis*
  • Phospholipids / chemistry
  • Sensitivity and Specificity

Substances

  • Epitopes
  • Gangliosides
  • Membranes, Artificial
  • Phospholipids
  • Pectins