Elmes, Robert B.P. and Jolliffe, Katrina A. (2014) Amino acid-based squaramides for anion recognition. Supramolecular Chemistry, 27 (5-6). pp. 321-328. ISSN 1061-0278

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Abstract

Eight receptors 1–8 comprising an l-lysine scaffold modified at N- and C-termini with aliphatic alkyl chains and N,N′-alkyl amides, respectively, and bearing squaramide moieties on the amino acid side chain were synthesised by a combination of solid- and solution-phase chemistries and shown to complex various anions in 0.5% H2O in dimethyl sulfoxide-d6 solution. All of the receptors were found to bind Cl− , AcO− and BzO− via hydrogen-bond or acid–base interactions with the squaramide protons; however, 1 was found to bind to via hydrogen bonds formed between the anion and both the squaramide and amide NH moieties. Moreover, modification of both the N- and C-termini of the amino acids with different alkyl substituents had a negligible effect on their anion-binding properties while simultaneously conferring lipophilicities in a range that is optimal for molecules to behave as ‘drug-like’ systems as defined by Lipinski's rule of five. The results of this study demonstrate the versatility of such amino acid receptors as building blocks in the field of anion recognition.

Item Type:	Article
Keywords:	anion binding; squaramide; amino acid;
Academic Unit:	Faculty of Science and Engineering > Chemistry
Item ID:	12533
Identification Number:	https://doi.org/10.1080/10610278.2014.976221
Depositing User:	Robert Elmes
Date Deposited:	06 Mar 2020 16:57
Journal or Publication Title:	Supramolecular Chemistry
Publisher:	Taylor & Francis
Refereed:	Yes
URI:	Publisher
Use Licence:	This item is available under a Creative Commons Attribution Non Commercial Share Alike Licence (CC BY-NC-SA). Details of this licence are available here

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