Fluorophore-labeled, peptide-based glycoclusters: Synthesis, binding properties for lectins, and detection of carbohydrate-binding proteins in cells

Xizhe Tian, Jaeyoung Pai, Kyung Hwa Baek, Sung Kyun Ko, Injae Shin

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

A facile and efficient solid-phase synthesis of linear peptide-based glycoclusters with various valences and different spatial arrangements of the sugar ligands is described. The synthetic strategy includes 1) solid-phase synthesis of fluorophore-labeled, alkyne-containing peptides, 2) coupling of azide-linked, unprotected mono-, di-, and trisaccharides to the alkyne-conjugated peptides on a solid support by click chemistry, and 3) release of the fluorophore-labeled glycoclusters from the solid support. By using this methodology, 32 fluorescent glycoclusters with a valence ranging from 1 to 4 and different spatial arrangements of the sugar ligands were prepared. Lectin-binding properties of the glycoclusters were initially examined by using microarrays immobilized by various lectins. These glycoclusters were then employed to detect the cell-surface carbohydrate-binding proteins in bacteria. Finally, the uptake of glycoclusters by mammalian cells through receptor-mediated endocytosis was evaluated. The results, obtained from the in vitro and in vivo studies, indicate that the binding affinities toward immobilized and cell-surface proteins are highly dependent on the valence and spatial arrangements of the sugar ligands in glycoclusters.

Original languageEnglish
Pages (from-to)2107-2113
Number of pages7
JournalChemistry - An Asian Journal
Volume6
Issue number8
DOIs
Publication statusPublished - 2011 Aug 1

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Organic Chemistry

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