Synthesis of an Fmoc-threonine bearing core-2 glycan: a building block for PSGL-1 via Fmoc-assisted solid-phase peptide synthesis.
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.
Krishnamurthy
Venkata R
VR
Department of Biomedical Engineering, Emory University/Georgia Institute of Technology, Atlanta, GA 30322, USA.
Dougherty
Ann
A
Kamat
Medha
M
Song
Xuezheng
X
Cummings
Richard D
RD
Chaikof
Elliot L
EL
D002240:Carbohydrate Sequence; D002384:Catalysis; D005449:Fluorenes / Q000737:chemistry*; D008562:Membrane Glycoproteins / Q000737:chemistry*; D008969:Molecular Sequence Data; D010446:Peptide Fragments / Q000138:chemical synthesis* / Q000737:chemistry*; D011134:Polysaccharides / Q000138:chemical synthesis* / Q000737:chemistry*; D013912:Threonine / Q000737:chemistry*
C496789:9-fluorenylmethoxycarbonyl; D005449:Fluorenes; D008562:Membrane Glycoproteins; C084882:P-selectin ligand protein; D010446:Peptide Fragments; D011134:Polysaccharides; D013912:Threonine