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