Synthesis of an Fmoc-threonine bearing core-2 glycan: a building block for PSGL-1 via Fmoc-assisted solid-phase peptide synthesis

Carbohydr Res. 2010 Jul 19;345(11):1541-7. doi: 10.1016/j.carres.2010.05.004. Epub 2010 May 12.

Abstract

Selectins (L, E, and P) are vascular endothelial molecules that play an important role in the recruitment of leukocytes to inflamed tissue. In this regard, P-Selectin glycoprotein-1 (PSGL-1) has been identified as a ligand for P-Selectin. PSGL-1 binds to P-Selectin through the interaction of core-2 O-glycan expressing sialyl Lewis(x) oligosaccharide and the three tyrosine sulfate residues. Herein, we report the synthesis of threonine-linked core-2 O-glycan as an amino acid building block for the synthesis of PSGL-1. This building block was further incorporated in the Fmoc-assisted solid-phase peptide synthesis to provide a portion of the PSGL-1 glycopeptide.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Sequence
  • Catalysis
  • Fluorenes / chemistry*
  • Membrane Glycoproteins / chemistry*
  • Molecular Sequence Data
  • Peptide Fragments / chemical synthesis*
  • Peptide Fragments / chemistry*
  • Polysaccharides / chemical synthesis*
  • Polysaccharides / chemistry*
  • Threonine / chemistry*

Substances

  • 9-fluorenylmethoxycarbonyl
  • Fluorenes
  • Membrane Glycoproteins
  • P-selectin ligand protein
  • Peptide Fragments
  • Polysaccharides
  • Threonine