Synthesis of the tumor associative α-aminooxy disaccharide of the TF antigen and its conjugation to a polysaccharide immune stimulant

Org Biomol Chem. 2014 Mar 21;12(11):1699-702. doi: 10.1039/c4ob00128a.

Abstract

The α-aminooxy derivative of the Thomsen-Friedenriech tumor associated carbohydrate antigen has been synthesized in 11 steps utilizing a D-GalN3 acceptor carrying a pre-installed α-N-hydroxysuccinimidyl moiety. The natural α linkage was prepared in high selectivity employing a suitably protected D-GalN3-thioglycoside donor with N-hydroxysuccinimide. With access to α-TF-ONH2, the preparation of the TF-PS A1 vaccine candidate ensued smoothly through oxime bond formation.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Adjuvants, Immunologic / chemistry
  • Disaccharides / chemical synthesis*
  • Disaccharides / chemistry
  • Polysaccharides / chemistry*
  • Polysaccharides / immunology

Substances

  • Adjuvants, Immunologic
  • Disaccharides
  • Polysaccharides