Enantioselective carbohydrate recognition by synthetic lectins in water

Pablo Ríos, Tiddo J. Mooibroek*, Tom S. Carter, Christopher Williams, Miriam R. Wilson, Matthew P. Crump, Anthony P. Davis

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

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Abstract

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.

Original languageEnglish
Pages (from-to)4056-4061
Number of pages6
JournalChemical Science
Volume8
Issue number5
Early online date30 Mar 2017
DOIs
Publication statusPublished - 1 May 2017

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Structured keywords

  • BrisSynBio
  • Bristol BioDesign Institute
  • BCS and TECS CDTs

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