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High-affinity anion binding by steroidal squaramide receptors

High-affinity anion binding by steroidal squaramide receptors
High-affinity anion binding by steroidal squaramide receptors
Exceptionally powerful anion receptors have been constructed by placing squaramide groups in axial positions on a steroidal framework. The steroid preorganizes the squaramide NH groups such that they can act cooperatively on a bound anion, while maintaining solubility in nonpolar media. The acidic NH groups confer higher affinities than previously-used ureas or thioureas. Binding constants exceeding 1014?M?1 have been measured for tetraethylammonium salts in chloroform by employing a variation of Cram’s extraction procedure. The receptors have also been studied as transmembrane anion carriers in unilamellar vesicles. Unusually their activities do not correlate with anion affinities, thus suggesting an upper limit for binding strength in the design of anion carriers
1433-7851
4592-4596
Edwards, Sophie J.
f852cb7b-4009-4b11-8a56-9d9451bd04a1
Valkenier, Hennie
b9599ae0-1740-495b-a00e-841e7552e1bc
Busschaert, Nathalie
bf307f09-0a86-4a03-afd8-4b0a59a8f72b
Gale, Philip A.
c840b7e9-6847-4843-91af-fa0f8563d943
Davis, Anthony P.
dc9078a1-2baf-4e8a-9baf-15cd06467541
Edwards, Sophie J.
f852cb7b-4009-4b11-8a56-9d9451bd04a1
Valkenier, Hennie
b9599ae0-1740-495b-a00e-841e7552e1bc
Busschaert, Nathalie
bf307f09-0a86-4a03-afd8-4b0a59a8f72b
Gale, Philip A.
c840b7e9-6847-4843-91af-fa0f8563d943
Davis, Anthony P.
dc9078a1-2baf-4e8a-9baf-15cd06467541

Edwards, Sophie J., Valkenier, Hennie, Busschaert, Nathalie, Gale, Philip A. and Davis, Anthony P. (2015) High-affinity anion binding by steroidal squaramide receptors. Angewandte Chemie International Edition, 54, 4592-4596. (doi:10.1002/anie.201411805).

Record type: Article

Abstract

Exceptionally powerful anion receptors have been constructed by placing squaramide groups in axial positions on a steroidal framework. The steroid preorganizes the squaramide NH groups such that they can act cooperatively on a bound anion, while maintaining solubility in nonpolar media. The acidic NH groups confer higher affinities than previously-used ureas or thioureas. Binding constants exceeding 1014?M?1 have been measured for tetraethylammonium salts in chloroform by employing a variation of Cram’s extraction procedure. The receptors have also been studied as transmembrane anion carriers in unilamellar vesicles. Unusually their activities do not correlate with anion affinities, thus suggesting an upper limit for binding strength in the design of anion carriers

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Accepted/In Press date: 15 January 2015
e-pub ahead of print date: 17 February 2015
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow

Identifiers

Local EPrints ID: 374497
URI: https://eprints.soton.ac.uk/id/eprint/374497
ISSN: 1433-7851
PURE UUID: 871a4232-4177-4da5-a7a4-ba27a7506f48
ORCID for Philip A. Gale: ORCID iD orcid.org/0000-0001-9751-4910

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Date deposited: 20 Feb 2015 09:18
Last modified: 17 Jul 2019 01:02

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