Acyclic pseudopeptidic hosts as molecular receptors and transporters for anions
Acyclic pseudopeptidic hosts as molecular receptors and transporters for anions
The synthesis and characterization of different pseudopeptidic hosts derived from open chain systems with C2 and C3 symmetry has been achieved. These receptors are based on structures containing phenylalanine amino acid residues and amine, amide, urea and thiourea groups as the structural elements providing their capability to interact with anions. The transport of chloride and organic anions of biological relevance (L-lactate, L-maleate and L-aspartate) through lipid bilayer membranes has been studied for these receptors. The chloride-binding properties of the selected hosts have been studied in solution by NMR titrations. In addition, in order to rationalize the results, lipophilicity studies have been carried out. It has been observed that transport activity is affected by the nature of the aliphatic central spacer and the side chains, the most active receptors being 9b, derived from a tripodal precursor with the shortest aliphatic side chain and 3c, derived from a bis(amino amide) but having the longest spacer. These hosts are more selective for the anion chloride than for the studied organic anions
supramolecular chemistry, host–guest systems, molecular recognition, receptors, anions, pseudopeptidic compounds
5150-5158
Martí, Inés
c53c5ff5-7e26-4541-94ad-c4974aab76e6
Burguete, M. Isabel
cc5f65c1-5e95-4b30-9d79-d6ac9b090b00
Gale, Philip A.
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Luis, Santiago V.
b176dfcf-0593-4a64-817e-b1b6e75f85a0
3 July 2015
Martí, Inés
c53c5ff5-7e26-4541-94ad-c4974aab76e6
Burguete, M. Isabel
cc5f65c1-5e95-4b30-9d79-d6ac9b090b00
Gale, Philip A.
c840b7e9-6847-4843-91af-fa0f8563d943
Luis, Santiago V.
b176dfcf-0593-4a64-817e-b1b6e75f85a0
Martí, Inés, Burguete, M. Isabel, Gale, Philip A. and Luis, Santiago V.
(2015)
Acyclic pseudopeptidic hosts as molecular receptors and transporters for anions.
European Journal of Organic Chemistry, .
(doi:10.1002/ejoc.201500390).
Abstract
The synthesis and characterization of different pseudopeptidic hosts derived from open chain systems with C2 and C3 symmetry has been achieved. These receptors are based on structures containing phenylalanine amino acid residues and amine, amide, urea and thiourea groups as the structural elements providing their capability to interact with anions. The transport of chloride and organic anions of biological relevance (L-lactate, L-maleate and L-aspartate) through lipid bilayer membranes has been studied for these receptors. The chloride-binding properties of the selected hosts have been studied in solution by NMR titrations. In addition, in order to rationalize the results, lipophilicity studies have been carried out. It has been observed that transport activity is affected by the nature of the aliphatic central spacer and the side chains, the most active receptors being 9b, derived from a tripodal precursor with the shortest aliphatic side chain and 3c, derived from a bis(amino amide) but having the longest spacer. These hosts are more selective for the anion chloride than for the studied organic anions
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e-pub ahead of print date: 3 July 2015
Published date: 3 July 2015
Keywords:
supramolecular chemistry, host–guest systems, molecular recognition, receptors, anions, pseudopeptidic compounds
Organisations:
Organic Chemistry: SCF
Identifiers
Local EPrints ID: 378712
URI: http://eprints.soton.ac.uk/id/eprint/378712
ISSN: 1434-193X
PURE UUID: 5e2b167a-9b98-40a4-9355-149f07fef504
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Date deposited: 09 Jul 2015 10:37
Last modified: 15 Mar 2024 03:06
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Contributors
Author:
Inés Martí
Author:
M. Isabel Burguete
Author:
Philip A. Gale
Author:
Santiago V. Luis
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