Synthesis of a neoglycoprotein containing the Lewis X analogous trisaccharide beta-D-GalpNAc-(1-->4)[alpha-L-Fucp-(1-->3)]-beta-D-GlcpNAc

Carbohydr Res. 1998 Jun;308(3-4):259-73. doi: 10.1016/s0008-6215(98)00082-2.

Abstract

The trisaccharide allyl glycoside 36 and related disaccharide part structures have been prepared using the 2-trichloroacetamido-2-deoxy-alpha-D-galactopyranosyl trichloroacetimidate derivative 9 as glycosyl donor under promotion with TMSOTf or Sn(OTf)2, respectively, to produce the beta-(1-->4) linkage to suitably protected glucosamine derivatives in fair yields. Fucosylation was effected employing the ethyl 1-thio glycosyl donor 20 in the presence of IDCP. Deprotection of the intermediates afforded the disaccharide allyl glycosides beta-D-GalpNAc-(1-->4)- beta-D-GlcpNAc 13, beta-D-GalpNClAc-(1-->4)-beta-D-GlcpNAc 14, alpha-L-Fucp-(1-->3)-beta-D-GlcpNAc 24, alpha-L-Fucp-(1-->4)-beta-D- GlcpNAc 31 and the branched trisaccharide allyl glycoside beta-D-GalpNAc-(1-->4)[alpha-L-Fucp-(1-->3)]-beta-D-GlcpNAc 36. The trisaccharide which corresponds to a structural motif occurring in N-glycoprotein glycans from human urokinase, human recombinant protein C, phospholipase A2 as well as O-glycans, was converted into a neoglycoprotein following introduction of a cysteamine-derived spacer group and subsequent activation with thiophosgene.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Sequence
  • E-Selectin / metabolism
  • Glycoproteins / chemical synthesis*
  • Glycosides / chemical synthesis
  • Humans
  • Ligands
  • Molecular Sequence Data
  • Nuclear Magnetic Resonance, Biomolecular
  • Oligosaccharides / metabolism
  • Phospholipases A / chemistry
  • Phospholipases A2
  • Polysaccharides / chemistry
  • Protein C / chemistry
  • Serum Albumin, Bovine / chemistry*
  • Sialyl Lewis X Antigen
  • Trisaccharides / chemical synthesis*
  • Urokinase-Type Plasminogen Activator / chemistry

Substances

  • E-Selectin
  • Glycoproteins
  • Glycosides
  • Ligands
  • N-acetylgalactosaminyl-1-4-(fucosopyranosyl-1-3)-N-acetylglucosamine
  • Oligosaccharides
  • Polysaccharides
  • Protein C
  • Sialyl Lewis X Antigen
  • Trisaccharides
  • Serum Albumin, Bovine
  • Phospholipases A
  • Phospholipases A2
  • Urokinase-Type Plasminogen Activator