Affinity enhancement by dendritic side chains in synthetic carbohydrate receptors

Harry Destecroix; Charles M. Renney; Tiddo J. Mooibroek; Tom S. Carter; Patrick F N Stewart; Matthew P. Crump; Anthony P. Davis

doi:10.1002/anie.201409124

Affinity enhancement by dendritic side chains in synthetic carbohydrate receptors

Harry Destecroix, Charles M. Renney, Tiddo J. Mooibroek, Tom S. Carter, Patrick F N Stewart, Matthew P. Crump, Anthony P. Davis

Research output: Contribution to journal › Article (Academic Journal) › peer-review

44 Citations (Scopus)

Abstract

Dendritic side chains have been used to modify the binding environment in anthracene-based synthetic carbohydrate receptors. Control of length, charge, and branching enabled the positioning of side-chain carboxylate groups in such a way that they assisted in binding substrates rather than blocking the cavity. Conformational degeneracy in the dendrimers resulted in effective preorganization despite the flexibility of the system. Strong binding was observed to glucosammonium ions in water, with Ka values up to 7000 m ^-1. Affinities for uncharged substrates (glucose and N-acetylglucosamine) were also enhanced, despite competition from solvent and the absence of electrostatic interactions.

Original language	English
Pages (from-to)	2057-5061
Number of pages	3005
Journal	Angewandte Chemie - International Edition
Volume	54
Issue number	7
DOIs	https://doi.org/10.1002/anie.201409124
Publication status	Published - 9 Feb 2015

Structured keywords

BCS and TECS CDTs

Keywords

Carbohydrates
Dendrimers
Molecular recognition
Receptors
Supramolecular chemistry

Access to Document

10.1002/anie.201409124

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2 Finished

3-month Core Capability for Chemistry Research
Crosby, J.
1/01/13 → 1/04/13
Project: Research
From "temples" to "courtyards" for carbohydrate recognition - expanding the scope of synthetic lectins.
Davis, A. P.
1/10/11 → 1/10/14
Project: Research

Professor Anthony P Davis
- Anthony.Davis@bristol.ac.uk
- Synthesis
- Supramolecular and Mechanistic Chemistry
- Catalysis
- Biological and Archaeological Chemistry
- School of Chemistry - Professor of Supramolecular Chemistry
Person: Academic , Member

Cite this

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title = "Affinity enhancement by dendritic side chains in synthetic carbohydrate receptors",

abstract = "Dendritic side chains have been used to modify the binding environment in anthracene-based synthetic carbohydrate receptors. Control of length, charge, and branching enabled the positioning of side-chain carboxylate groups in such a way that they assisted in binding substrates rather than blocking the cavity. Conformational degeneracy in the dendrimers resulted in effective preorganization despite the flexibility of the system. Strong binding was observed to glucosammonium ions in water, with Ka values up to 7000 m -1. Affinities for uncharged substrates (glucose and N-acetylglucosamine) were also enhanced, despite competition from solvent and the absence of electrostatic interactions.",

keywords = "Carbohydrates, Dendrimers, Molecular recognition, Receptors, Supramolecular chemistry",

author = "Harry Destecroix and Renney, {Charles M.} and Mooibroek, {Tiddo J.} and Carter, {Tom S.} and Stewart, {Patrick F N} and Crump, {Matthew P.} and Davis, {Anthony P.}",

year = "2015",

month = feb,

day = "9",

doi = "10.1002/anie.201409124",

language = "English",

volume = "54",

pages = "2057--5061",

journal = "Angewandte Chemie - International Edition",

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}

Affinity enhancement by dendritic side chains in synthetic carbohydrate receptors. / Destecroix, Harry; Renney, Charles M.; Mooibroek, Tiddo J.; Carter, Tom S.; Stewart, Patrick F N; Crump, Matthew P.; Davis, Anthony P.

In: Angewandte Chemie - International Edition, Vol. 54, No. 7, 09.02.2015, p. 2057-5061.

Research output: Contribution to journal › Article (Academic Journal) › peer-review

TY - JOUR

T1 - Affinity enhancement by dendritic side chains in synthetic carbohydrate receptors

AU - Destecroix, Harry

AU - Renney, Charles M.

AU - Mooibroek, Tiddo J.

AU - Carter, Tom S.

AU - Stewart, Patrick F N

AU - Crump, Matthew P.

AU - Davis, Anthony P.

PY - 2015/2/9

Y1 - 2015/2/9

N2 - Dendritic side chains have been used to modify the binding environment in anthracene-based synthetic carbohydrate receptors. Control of length, charge, and branching enabled the positioning of side-chain carboxylate groups in such a way that they assisted in binding substrates rather than blocking the cavity. Conformational degeneracy in the dendrimers resulted in effective preorganization despite the flexibility of the system. Strong binding was observed to glucosammonium ions in water, with Ka values up to 7000 m -1. Affinities for uncharged substrates (glucose and N-acetylglucosamine) were also enhanced, despite competition from solvent and the absence of electrostatic interactions.

AB - Dendritic side chains have been used to modify the binding environment in anthracene-based synthetic carbohydrate receptors. Control of length, charge, and branching enabled the positioning of side-chain carboxylate groups in such a way that they assisted in binding substrates rather than blocking the cavity. Conformational degeneracy in the dendrimers resulted in effective preorganization despite the flexibility of the system. Strong binding was observed to glucosammonium ions in water, with Ka values up to 7000 m -1. Affinities for uncharged substrates (glucose and N-acetylglucosamine) were also enhanced, despite competition from solvent and the absence of electrostatic interactions.

KW - Carbohydrates

KW - Dendrimers

KW - Molecular recognition

KW - Receptors

KW - Supramolecular chemistry

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U2 - 10.1002/anie.201409124

DO - 10.1002/anie.201409124

M3 - Article (Academic Journal)

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AN - SCOPUS:84922311196

VL - 54

SP - 2057

EP - 5061

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

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ER -

Affinity enhancement by dendritic side chains in synthetic carbohydrate receptors

Abstract

Structured keywords

Keywords

Access to Document

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3-month Core Capability for Chemistry Research

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

Professor Anthony P Davis

Cite this