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Glycoconjugate Journal

, Volume 22, Issue 3, pp 95–108 | Cite as

6-O-Sulfo sialylparagloboside and sialyl Lewis X neo-glycolipids containing lactamized neuraminic acid: Synthesis and antigenic reactivity against G159 monoclonal antibody

  • Masanori Yamaguchi
  • Hideharu Ishida
  • Akiko Kanamori
  • Reiji Kannagi
  • Makoto Kiso
Article

Abstract

Synthesis and antigenic reactivity of 6-O-sulfo sialylparagloboside (SPG) and sialyl Lewis X (sLe X ) neo-glycolipids containing lactamized neuraminic acid are described. The suitably protected GlcNAc-β (1 → 3)-Gal-β (1 → 4)-GlcOSE derivative was glycosylated with NeuTFAc-α (2 → 3)-Gal imidate to give NeuTFAc-α (2 → 3)-Galβ (1 → 4)-GlcNAc-β (1 → 3)-Gal-β (1 → 4)-GlcOSE pentasaccharide. The partial N,O-deacylation in the NeuTFAc-α (2→3)-Gal part afforded N-deacetylated SPG derivative which was converted to the desired oligosaccharide containing lactamized neuraminic acid. Similar treatment of the sLeX hexasaccharide derivative, NeuTFAc-α (2 → 3)-Gal-β (1 → 4) [Fuc-α (1 →3)]-GlcNAc-β (1 → 3)-Gal-β (1 → 4)-GlcOSE, gave the key hexasaccharide intermediate containing lactamized neuraminic acid. These suitably protected SPG and sLex oligosaccharides were converted stepwise into the desired neo-glycolipids (GSC-551 and GSC-552) by the coupling with 2-(tetradecyl)hexadecanol, 6-O-sulfation at C-6 of the GlcNAc residure, and complete deprotection.

Both lactamized-sialyl 6-O-sulfo SPG (GSC-551) and sLex (GSC-552) neo-glycolipids were clearly recognized with G159 monoclonal antibody showing that both the lactamized neuraminic acid and the 6-O-sulfate at C-6 of GlcNAc would be involved in the G159-defined determinant. However, the Fuc residue and the lipophilic (ceramide) part may not be critical for this recognition. Published in 2005

Selectin glycolipid sialic acid sialyl Lewis X sialylparagloboside carbohydrate antibody sulfation 

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Copyright information

© Springer Science + Business Media, Inc. 2005

Authors and Affiliations

  • Masanori Yamaguchi
    • 1
    • 4
  • Hideharu Ishida
    • 1
  • Akiko Kanamori
    • 2
  • Reiji Kannagi
    • 2
    • 3
  • Makoto Kiso
    • 1
    • 3
  1. 1.Department of Applied Bio-Organic ChemistryGifu UniversityGifuJapan
  2. 2.Department of Molecular PathologyResearch Institute, Aichi Cancer CenterChikusakuJapan
  3. 3.CRESTJapan Science and Technology Corporation (JST)TokyoJapan
  4. 4.Faculty of Applied Biological SciencesGifu UniversityGifuJapan

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