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Neoglycolipid probes prepared via oxime ligation for microarray analysis of oligosaccharide-protein interactions

Liu, Y., Feizi, T., Carnpanero-Rhodes, M.A., Childs, R.A., Zhang, Y.N., Muiioy, B., Evans, P.G., Osborn, H.M.I., Otto, D., Crocker, P.R. and Chai, W.C. (2007) Neoglycolipid probes prepared via oxime ligation for microarray analysis of oligosaccharide-protein interactions. Chemistry & Biology, 14 (7). pp. 847-859. ISSN 1074-5521

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To link to this article DOI: 10.1016/j.chembiol.2007.06.009

Abstract/Summary

Neoglycolipid technology is the basis of a microarray platform for assigning oligosaccharide ligands for carbohydrate-binding proteins. The strategy for generating the neoglycolipid probes by reductive amination results in ring opening of the core monosaccharides. This often limits applicability to short-chain saccharides, although the majority of recognition motifs are satisfactorily presented with neoglycolipids of longer oligosaccharides. Here, we describe neoglycolipids prepared by oxime ligation. We provide evidence from NMR studies that a significant proportion of the oxime-linked core monosaccharide is in the ring-closed form, and this form selectively interacts with a carbohydrate-binding protein. By microarray analyses we demonstrate the effective presentation with oxime-linked neoglycolipids of (1) Lewis(x) trisaccharide to antibodies to Lewisx, (2) sialyllactose analogs to the sialic acid-binding receptors, siglecs, and (3) N-glycans to a plant lectin that requires an intact N-acetylglucosamine core.

Item Type:Article
Refereed:Yes
Divisions:Faculty of Life Sciences > School of Chemistry, Food and Pharmacy > Department of Chemistry
Faculty of Life Sciences > School of Chemistry, Food and Pharmacy > School of Pharmacy
ID Code:13700
Uncontrolled Keywords:CARBOHYDRATE MICROARRAYS, CHEMOSELECTIVE LIGATION, MASS-SPECTROMETRY, GLYCANS, BINDING, DERIVATIVES, GLYCOMICS, LECTINS, COMPLEX, SIALOADHESIN

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