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Synthesis and anion-binding properties of new disulfonamide-based receptors

Synthesis and anion-binding properties of new disulfonamide-based receptors
Synthesis and anion-binding properties of new disulfonamide-based receptors
The synthesis of disulfonamide receptor scaffolds for anion binding is reported. Acyclic receptors are found to tightly bind acetate in MeCN-d3 with dominant 1:1 stoichiometry, a smaller, sequential 1:2 (H+G) association is also found. Constraint of the disulfonamide receptor into macrocycles serves to eliminate the 1:2 binding stoichiometry and X-ray crystal structures of several macrocyclic receptors allow rationalisation of their affinity for acetate binding. l-Valine derived macrocycles maintain tight 1:1 binding of acetate (Ka1:1 >104 M?1) in MeCN-d3 and display preference for oxyanion binding in more competitive MeCN-d3/2% H2O.

0040-4020
2184-2195
Mammoliti, Oscar
d155a8cd-1495-400a-a159-10e75d0d6598
Allasia, Sara
14bc5525-1e6d-4749-bd76-54c09fc79a68
Dixon, Sally
943160fc-1b70-4c29-b2e3-b7785cee8a0c
Kilburn, Jeremy D.
e64ded70-825a-40ec-816b-c4605e007e7a
Mammoliti, Oscar
d155a8cd-1495-400a-a159-10e75d0d6598
Allasia, Sara
14bc5525-1e6d-4749-bd76-54c09fc79a68
Dixon, Sally
943160fc-1b70-4c29-b2e3-b7785cee8a0c
Kilburn, Jeremy D.
e64ded70-825a-40ec-816b-c4605e007e7a

Mammoliti, Oscar, Allasia, Sara, Dixon, Sally and Kilburn, Jeremy D. (2009) Synthesis and anion-binding properties of new disulfonamide-based receptors. Tetrahedron, 65 (11), 2184-2195. (doi:10.1016/j.tet.2009.01.070).

Record type: Article

Abstract

The synthesis of disulfonamide receptor scaffolds for anion binding is reported. Acyclic receptors are found to tightly bind acetate in MeCN-d3 with dominant 1:1 stoichiometry, a smaller, sequential 1:2 (H+G) association is also found. Constraint of the disulfonamide receptor into macrocycles serves to eliminate the 1:2 binding stoichiometry and X-ray crystal structures of several macrocyclic receptors allow rationalisation of their affinity for acetate binding. l-Valine derived macrocycles maintain tight 1:1 binding of acetate (Ka1:1 >104 M?1) in MeCN-d3 and display preference for oxyanion binding in more competitive MeCN-d3/2% H2O.

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Published date: 14 March 2009

Identifiers

Local EPrints ID: 176353
URI: http://eprints.soton.ac.uk/id/eprint/176353
ISSN: 0040-4020
PURE UUID: 04968514-9f06-4f26-97be-65a769921c41
ORCID for Sally Dixon: ORCID iD orcid.org/0000-0003-2219-3635

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Date deposited: 08 Mar 2011 11:43
Last modified: 19 Nov 2019 01:50

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Contributors

Author: Oscar Mammoliti
Author: Sara Allasia
Author: Sally Dixon ORCID iD
Author: Jeremy D. Kilburn

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