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Glycobiology Advance Access published online on July 2, 2007
Glycobiology, doi:10.1093/glycob/cwm069
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© The Author 2007. Published by Oxford University Press. All rights reserved. For permissions, please e-mail: journals.permissions@oxfordjournals.org

Self-recognition of N-linked glycans with multivalent GlcNAc, determined as ceramide mimetic conjugate*

Seon-Joo Yoon1, Shoko Ikeda2, Martin Sadilek3, Sen-itiroh Hakomori1, Hideharu Ishida2 and Makoto Kiso2

1 Division of Biomembrane Research, Pacific Northwest Research Institute, and Dept. of Pathobiology, University of Washington, Seattle, WA 98122, USA
2 Dept of Applied Bio-organic Chemistry, Gifu Univ, Gifu 501-1193, Japan
3 Dept. of Chemistry, University of Washington, Seattle, WA 98195, USA

Received on May 15, 2007; accepted on June 20, 2007

Aminoceramide mimetic was synthesized and conjugated to N-linked oligosaccharides having multivalent GlcNAc by reductive amination. Ceramide mimetic conjugates with "complex-type" glycan having 5 or 6 GlcNAc termini (termed Os Fr. B-Cer) were purified, analyzed by thin-layer chromatography, and finally characterized by MS/MS analysis through liquid chromatography/mass spectrometry. Binding of Os Fr. B-Cer placed on solid phase polystyrene surface with [3H]cholesterol-labeled liposomes containing Os Fr. B-Cer, or containing various glycosphingolipids was determined. The binding of Os Fr. B-Cer liposomes to Os Fr. B-Cer coated plate was significantly higher than binding of GM3 liposomes. Other glycosphingolipid liposomes showed no binding. Thus, self-recognition of Os Fr. B-Cer was clearly demonstrated using ceramide mimetic conjugates.

Key words: carbohydrate-to-carbohydrate interaction / homotypic interaction / oligosaccharide / aminoceramide / multivalent GlcNAc / glycosphingolipid

* This investigation has been supported by NIH/National Institute of General Medical Science (R01 GM070593) to S.H., and by the Ministry of Education, Culture, Sports, Science, and Technology (MEXT) of Japan (Grant-in-Aid for Scientific Research, No. 17101007, to M.K.).


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