Projects per year
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 |
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Pages (from-to) | 2057-5061 |
Number of pages | 3005 |
Journal | Angewandte Chemie - International Edition |
Volume | 54 |
Issue number | 7 |
DOIs | |
Publication status | Published - 9 Feb 2015 |
Structured keywords
- BCS and TECS CDTs
Keywords
- Carbohydrates
- Dendrimers
- Molecular recognition
- Receptors
- Supramolecular chemistry
Fingerprint
Dive into the research topics of 'Affinity enhancement by dendritic side chains in synthetic carbohydrate receptors'. Together they form a unique fingerprint.Projects
- 2 Finished
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From "temples" to "courtyards" for carbohydrate recognition - expanding the scope of synthetic lectins.
1/10/11 → 1/10/14
Project: Research
Profiles
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Professor Anthony P Davis
- School of Chemistry - Professor of Supramolecular Chemistry
- Synthesis
- Supramolecular and Mechanistic Chemistry
- Catalysis
- Biological and Archaeological Chemistry
Person: Academic , Member