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Molecules 2015, 20(2), 3354-3370; doi:10.3390/molecules20023354

Investigation of Structural Mimetics of Natural Phosphate Ion Binding Motifs

Institute of Chemistry, Faculty of Natural Sciences, Technische Universität Chemnitz, 09107 Chemnitz, Germany
These authors contributed equally to this work.
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Author to whom correspondence should be addressed.
Academic Editor: David B. Smithrud
Received: 27 December 2014 / Revised: 19 January 2015 / Accepted: 12 February 2015 / Published: 16 February 2015
(This article belongs to the Special Issue Host-Guest Chemistry)
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Abstract

Phosphates are ubiquitous in biology and nearly half of all proteins interact with their partners by means of recognition of phosphate residues. Therefore, a better understanding of the phosphate ion binding by peptidic structures is highly desirable. Two new receptors have been designed and synthesized and their anion binding properties in an acetonitrile solution have been determined. The structure of hosts mimics a part of the kinase active site that is responsible for the recognition of the phosphate residue. New hosts contain additional free amino groups with the aim to facilitate coordination of protonated anions, such as dihydrogen phosphate. According to spectrophotometric measurements, stepwise 1:1 and 1:2 binding modes have been observed for both receptors in the presence of acetate, hydrogen sulfate and dihydrogen phosphate. Compared with the acyclic receptor, the macrocyclic receptor has demonstrated a remarkably enhanced selectivity for dihydrogen phosphate over other anions. Fluorometric measurements have revealed different responses of the acyclic and macrocyclic receptors towards anions. However, in both cases, a 5–8 nm hypsochromic shift of fluorescence maximum has been observed upon interaction of acetate and dihydrogen phosphate with receptors. View Full-Text
Keywords: phosphate binding; peptide mimetics; macrocycle; glycine-rich loop; synthetic receptor; host-guest chemistry; anion binding phosphate binding; peptide mimetics; macrocycle; glycine-rich loop; synthetic receptor; host-guest chemistry; anion binding
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Kataev, E.A.; Shumilova, T.A. Investigation of Structural Mimetics of Natural Phosphate Ion Binding Motifs. Molecules 2015, 20, 3354-3370.

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