Synthesis of allyl glycosides for conversion into neoglycoproteins bearing epitopes of mycobacterial glycolipid antigens

Carbohydr Res. 1991 Sep 2:216:337-55. doi: 10.1016/0008-6215(92)84172-o.

Abstract

Neoglycoproteins bearing key glycosyl substituents of several glycopeptidolipid antigens of pathogenic Mycobacterium species have been synthesized. Allyl glycosides of the terminal 6-deoxyhexose-containing units of the antigens were prepared, with appropriate ether and ester substituents in place. Ozonolysis of the allyl glycosides was then followed by reductive coupling with epsilon-amino groups of lysine residues in bovine serum albumin, using sodium cyanoborohydride at pH 7.8. The resulting neoglycoproteins emulated the antigenicity of the native molecule in several serological tests.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Antigens, Bacterial / chemistry*
  • Carbohydrate Sequence
  • Epitopes / chemistry
  • Glycolipids / chemistry
  • Glycolipids / immunology
  • Glycoproteins / chemical synthesis*
  • Glycoproteins / chemistry
  • Glycoproteins / immunology*
  • Glycosides / chemical synthesis*
  • Glycosides / chemistry
  • Molecular Sequence Data
  • Molecular Structure
  • Mycobacterium avium Complex / immunology

Substances

  • Antigens, Bacterial
  • Epitopes
  • Glycolipids
  • Glycoproteins
  • Glycosides