Synthesis of fragments of the glycocalyx glycan of the parasite Schistosoma mansoni

Chemistry. 2002 Jan 4;8(1):151-61. doi: 10.1002/1521-3765(20020104)8:1<151::aid-chem151>3.0.co;2-c.

Abstract

The chemical synthesis of alpha-L-Fucp-(1 --> 3)-beta-D-GalpNAc-(1 --> 4)-beta-D-GlcpNAc-(1 --> 3)-alpha-D-GalpO(CH2)5NH2, beta-D-GalpNAc-(1 --> 4)-[alpha-L-Fucp-(1 --> 3)-]beta-D-GlcpNAc-(1 --> 3)-alpha-D-GalpO(CH2)5NH2, and alpha-L-Fucp-(1 --> 3)-beta-D-GalpNAc-(1 --> 4)-[alpha-L-Fucp-(1 --> 3)-]beta-D-GlcpNAc-(1 --> 3)-alpha-D-GalpO(CH2)5NH2 is described. These structures represent fucosylated oligosaccharide fragments of the glycocalyx glycan of the cercarial stage of the parasite Schistosoma mansoni, and in protein-conjugated form they are potential diagnostics in the search for antibodies raised against the glycan in the serum of infected humans.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antibodies, Protozoan / blood
  • Catalysis
  • Chemical Phenomena
  • Chemistry, Physical
  • Fucose / analogs & derivatives
  • Fucose / chemistry
  • Galactose / analogs & derivatives
  • Galactose / chemistry
  • Glucose / analogs & derivatives
  • Glucose / chemistry
  • Glycosylation
  • Humans
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Oligosaccharides / chemical synthesis*
  • Oligosaccharides / chemistry*
  • Polysaccharides / chemical synthesis*
  • Polysaccharides / chemistry
  • Schistosoma mansoni / chemistry*
  • Spectrophotometry, Infrared

Substances

  • Antibodies, Protozoan
  • Oligosaccharides
  • Polysaccharides
  • Fucose
  • Glucose
  • Galactose