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Glycobiology Advance Access originally published online on July 2, 2007
Glycobiology 2007 17(9):1007-1014; 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
This is an Open Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/by-nc/2.0/uk/) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.

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

Seon-Joo Yoon2, Shoko Ikeda4, Martin Sadilek3, Sen-itiroh Hakomori1,2, Hideharu Ishida4 and Makoto Kiso4

2 Division of Biomembrane Research, Pacific Northwest Research Institute, Department of Pathobiology, University of Washington, Seattle, WA 98195, USA
3 Department of Chemistry, University of Washington, Seattle, WA 98195, USA
4 Department of Applied Bio-organic Chemistry, Gifu University, Gifu 501-1193, Japan

1 Author to whom correspondence should be addressed: Sen-itiroh Hakomori, Pacific Northwest Research Institute, 720 Broadway, Seattle, WA 98122-4302; E-mail: hakomori{at}u.washington.edu; Tel: +1 206 726 1222; Fax: +1 206 726 1212

Received on May 15, 2007; revised on June 12, 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 five or six GlcNAc termini (termed Os Fr. B-Cer) were purified, analyzed by thin-layer chromatography (TLC), 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 glyco- sphingolipids (GSLs) 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 GSL liposomes showed no binding. Thus, self-recognition of Os Fr. B-Cer was clearly demonstrated using ceramide mimetic conjugates.

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


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