A Synthetic Lectin for O-Linked β-N-Acetylglucosamine (O-GlcNAc)

Y. Ferrand, E. Klein, N. P. Barwell, M. P. Crump, J. Jiménez-Barbero, C. Vicent, G.-J. Boons, S. Ingale, A. P. Davis*

Angew. Chem. Int. Ed. 2009, 49, 1775

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Changing employment: Receptor 1 binds β-N-acetylglucosaminyl (β-GlcNAc) up to 100 times more strongly than it does glucose. This synthetic lectin shows affinities similar to wheat germ agglutinin (WGA), a natural lectin used to bind GlcNAc. Remarkably, 1 is more selective than WGA. It favors especially the glycoside unit in glycopeptide 2, a model of the serine-O-GlcNAc posttranslational protein modification.