Synthesis and binding analysis of unique AG2 pentasaccharide to human Siglec-2 using NMR techniques

Shinya Hanashima, Ken ichi Sato, Yuko Naito, Hiromu Takematsu, Yasunori Kozutsumi, Yukishige Ito, Yoshiki Yamaguchi

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Siglec-2 is a mammalian sialic acid binding protein expressed on B-cell surfaces and is involved in the modulation of B-cell mediated immune response. We synthesized a unique starfish ganglioside, AG2 pentasaccharide Galfβ(1-3)Galpα(1-4)Neu5Acα(2-3)Galpβ(1-4)Glcp, and found that the synthetic pentasaccharide binds to human Siglec-2 by performing 1H NMR experiments. Saturation transfer difference NMR experiments indicated that the C7-C9 side-chain and the acetamide moiety of the central sialic acid residue were located in the binding face of human Siglec-2. We determined the binding epitope of AG2 pentasaccharide to human Siglec-2, as the Galpα(1-4)Neu5Acα(2-3)Galp unit.

Original languageEnglish
Pages (from-to)3720-3725
Number of pages6
JournalBioorganic and Medicinal Chemistry
Volume18
Issue number11
DOIs
Publication statusPublished - 01-06-2010
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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