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

doi:10.1039/c6sc05399h

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 journal › Article (Academic Journal) › peer-review

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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 K_a 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 K_a = 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 language	English
Pages (from-to)	4056-4061
Number of pages	6
Journal	Chemical Science
Volume	8
Issue number	5
Early online date	30 Mar 2017
DOIs	https://doi.org/10.1039/c6sc05399h
Publication status	Published - 1 May 2017

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BrisSynBio
Bristol BioDesign Institute
BCS and TECS CDTs

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10.1039/c6sc05399h

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This is the final published version of the article (version of record). It first appeared online via the Royal Society of Chemistry at https://doi.org/10.1039/C6SC05399H . Please refer to any applicable terms of use of the publisher.
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This is the final published version of the article (version of record). It first appeared online via the Royal Society of Chemistry at https://doi.org/10.1039/C6SC05399H . Please refer to any applicable terms of use of the publisher.
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A 13C NMR Coldprobe to Underpin Chemistry Research.
Butts, C. P. (Principal Investigator)
28/02/14 → 29/11/17
Project: Research
3-month Core Capability for Chemistry Research
Crosby, J. (Principal Investigator)
1/01/13 → 1/04/13
Project: Research
From "temples" to "courtyards" for carbohydrate recognition - expanding the scope of synthetic lectins.
Davis, A. P. (Principal Investigator)
1/10/11 → 1/10/14
Project: Research

Professor Matthew P Crump
- Matt.Crumpbristol.acuk
- School of Chemistry - Professor of NMR and Structural Biology
- Cancer
Person: Academic , Member
Professor Anthony P Davis
- Anthony.Davisbristol.acuk
- School of Chemistry - Professor of Supramolecular Chemistry
Person: Academic

Cite this

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title = "Enantioselective carbohydrate recognition by synthetic lectins in water",

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.",

author = "Pablo R{\'i}os and Mooibroek, {Tiddo J.} and Carter, {Tom S.} and Christopher Williams and Wilson, {Miriam R.} and Crump, {Matthew P.} and Davis, {Anthony P.}",

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T1 - Enantioselective carbohydrate recognition by synthetic lectins in water

AU - Ríos, Pablo

AU - Mooibroek, Tiddo J.

AU - Carter, Tom S.

AU - Williams, Christopher

AU - Wilson, Miriam R.

AU - Crump, Matthew P.

AU - Davis, Anthony P.

PY - 2017/5/1

Y1 - 2017/5/1

N2 - 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.

AB - 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.

U2 - 10.1039/c6sc05399h

DO - 10.1039/c6sc05399h

M3 - Article (Academic Journal)

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SP - 4056

EP - 4061

JO - Chemical Science

JF - Chemical Science

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ER -

Enantioselective carbohydrate recognition by synthetic lectins in water

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Projects

A 13C NMR Coldprobe to Underpin Chemistry Research.

3-month Core Capability for Chemistry Research

From "temples" to "courtyards" for carbohydrate recognition - expanding the scope of synthetic lectins.

Profiles

Professor Matthew P Crump

Professor Anthony P Davis

Cite this