Recognition of Amino Acid Salts by Temperature‐Dependent Allosteric Binding with Stereodynamic Urea Receptors
Abstract: Positive homotropic artificial allosteric systems are important for the regulation of cooperativity, selectivity and nonlinear amplification. Stereodynamic homotropic allosteric receptors can transmit and amplify induced chirality by the first ligand binding to axial chirality between two chromophores. We herein report stereodynamic allosteric urea receptors consisting of a rotational shaft as the axial chirality unit, terphenyl units as structural transmission sites and four urea units as binding sites. NMR titration experiments revealed that the receptor can bind two carboxylate guests in a positive homotropic allosteric manner attributed to the inactivation by intramolecular hydrogen‐bonding between urea units within the receptor. In addition, the VT‐CD spectra observed upon binding of the urea receptor with l‐ or d‐amino acid salts in MeCN showed interesting temperature‐dependent Cotton effects, based on the differences of the receptor shaft unit and the guest structure. The successful discrimination of hydrocarbon‐based side chains of amino acid salts indicated that the input of chiral and steric information for the guest was amplified as outputs of the Cotton effect and the temperature‐dependence of VT‐CD spectra through cooperativity of positive allosteric binding.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Recognition of Amino Acid Salts by Temperature‐Dependent Allosteric Binding with Stereodynamic Urea Receptors ; day:09 ; month:04 ; year:2024 ; extent:10
Chemistry - a European journal ; (09.04.2024) (gesamt 10)
- Creator
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Kimura, Yuki
Matsumura, Kotaro
Ono, Kosuke
Tsuchido, Yoshitaka
Kawai, Hidetoshi
- DOI
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10.1002/chem.202400154
- URN
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urn:nbn:de:101:1-2024041014292790617549
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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14.08.2025, 10:46 AM CEST
Data provider
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Kimura, Yuki
- Matsumura, Kotaro
- Ono, Kosuke
- Tsuchido, Yoshitaka
- Kawai, Hidetoshi
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