Issue 5, 2017

Enantioselective carbohydrate recognition by synthetic lectins in water


Carbohydrate receptors with a chiral framework have been generated by combining a tetra-aminopyrene and a C3-symmetrical triamine via isophthalamide spacers bearing water-solubilising groups. These “synthetic lectins” are the first to show enantiodiscrimination in aqueous solution, binding N-acetylglucosamine (GlcNAc) with 16 : 1 enantioselectivity. They also show exceptional affinities. GlcNAc is bound with Ka up to 1280 M−1, more than twice that measured for previous synthetic lectins, and three times the value for wheat germ agglutinin, the lectin traditionally employed to bind GlcNAc in glycobiological research. Glucose is bound with Ka = 250 M−1, again higher than previous synthetic lectins. The results suggest that chirality can improve complementarity to carbohydrate substrates and may thus be advantageous in synthetic lectin design.

Graphical abstract: Enantioselective carbohydrate recognition by synthetic lectins in water

Supplementary files

Article information

Article type
Edge Article
09 Dec 2016
28 Mar 2017
First published
30 Mar 2017
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2017,8, 4056-4061

Enantioselective carbohydrate recognition by synthetic lectins in water

P. Ríos, T. J. Mooibroek, T. S. Carter, C. Williams, M. R. Wilson, M. P. Crump and A. P. Davis, Chem. Sci., 2017, 8, 4056 DOI: 10.1039/C6SC05399H

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