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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.

SUBMITTER: Krishnamurthy VR

PROVIDER: S-EPMC2902660 | biostudies-literature | 2010 Jul

REPOSITORIES: biostudies-literature

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

Krishnamurthy Venkata R VR Dougherty Ann A Kamat Medha M Song Xuezheng X Cummings Richard D RD Chaikof Elliot L EL

Carbohydrate research 20100512 11

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 ...[more]

PMID: 20561607

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