Synthesis and NMR assignments of galactosylgloboside and its beta-D-GalNAc-(1-->4)-alpha-D-Gal-linked positional isomer in a conjugatable form

Carbohydr Res. 1999 Feb 28;315(3-4):251-61. doi: 10.1016/s0008-6215(99)00018-x.

Abstract

Two pentasaccharides suitable for conjugation, namely 3-aminopropyl glactosylgloboside and its beta-D-GalNAc-(1-->4)-alpha-D-Gal-linked positional isomer, were synthesized from 3III,4III-di-O-unprotected globotrioside and the trichloroacetimidate of beta-D-Gal-(1-->3)-beta-D-GalNPhth derivative. Glycosylation at both positions led to the formation of beta-D-GalNPhth-(1-->4)-alpha-D-Gal and beta-D-GalNPhth-(1-->3)-alpha-D-Gal-linked products in a ratio of 1:1 without selectivity. Complete NMR spectral assignments are also described.

MeSH terms

  • Antigens, Tumor-Associated, Carbohydrate
  • Carbohydrate Sequence
  • Glycosphingolipids / chemical synthesis*
  • Glycosphingolipids / chemistry
  • Isomerism
  • Magnetic Resonance Spectroscopy
  • Molecular Sequence Data
  • Stage-Specific Embryonic Antigens

Substances

  • Antigens, Tumor-Associated, Carbohydrate
  • Glycosphingolipids
  • Stage-Specific Embryonic Antigens
  • stage-specific embryonic antigen-3