6-<Emphasis Type="Italic">O</Emphasis>-Sulfo sialylparagloboside and sialyl Lewis X neo-glycolipids containing lactamized neuraminic acid: Synthesis and antigenic reactivity against G159 monoclonal antibody |
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Authors: | Masanori?Yamaguchi Email author" target="_blank">Hideharu?IshidaEmail author Akiko?Kanamori Reiji?Kannagi Makoto?Kiso |
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Institution: | (1) Department of Applied Bio-Organic Chemistry, Gifu University, Gifu 501-1193, Japan;(2) Department of Molecular Pathology, Research Institute, Aichi Cancer Center, 1-1 Kanokoden, Chikusaku Nagoya, 464-8681, Japan;(3) CREST, Japan Science and Technology Corporation (JST), Tokyo, Japan;(4) Division of Life Science, Graduate School of Biostudies, Kyoto University, Sakyo-ku Kyoto, 606-8502, Japan;(5) Faculty of Applied Biological Sciences, Gifu University, Gifu 501-1193, Japan |
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Abstract: | Synthesis and antigenic reactivity of 6-O-sulfo sialylparagloboside (SPG) and sialyl Lewis X (sLeX) 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 2005Synthetic studies on sialoglycoconjugates, Part 138. For part 136, see Ref 1], and for part 137, see Ref 19]. |
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Keywords: | Selectin glycolipid sialic acid sialyl Lewis X sialylparagloboside carbohydrate antibody sulfation |
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