Transmembrane Fluoride Transport by a Cyclic Azapeptide With Two β-Turns
Autor: | Miaomiao Zhang, Peimin Weng, Bailing Tang, Yueyang Zhang, Zhao Li, Yun-Bao Jiang, Zhixing Zhao, Xiao-Sheng Yan |
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Jazyk: | angličtina |
Rok vydání: | 2021 |
Předmět: |
transmembrane transport
genetic structures Peptide behavioral disciplines and activities Chloride lcsh:Chemistry chemistry.chemical_compound β-turn medicine Lipid bilayer cyclic azapeptide Original Research chemistry.chemical_classification fluoride Chemistry Hydrogen bond General Chemistry Membrane transport ion recognition Combinatorial chemistry Transmembrane protein nervous system Thiourea lcsh:QD1-999 Fluoride psychological phenomena and processes medicine.drug |
Zdroj: | Frontiers in Chemistry, Vol 8 (2021) Frontiers in Chemistry |
ISSN: | 2296-2646 |
Popis: | Diverse classes of anion transporters have been developed, most of which focus on the transmembrane chloride transport due to its significance in living systems. Fluoride transport has, to some extent, been overlooked despite the importance of fluoride channels in bacterial survival. Here, we report the design and synthesis of a cyclic azapeptide (a peptide-based N-amidothiourea, 1), as a transporter for fluoride transportation through a confined cavity that encapsulates fluoride, together with acyclic control compounds, the analogs 2 and 3. Cyclic receptor 1 exhibits more stable β-turn structures than the control compounds 2 and 3 and affords a confined cavity containing multiple inner –NH protons that serve as hydrogen bond donors to bind anions. It is noteworthy that the cyclic receptor 1 shows the capacity to selectively transport fluoride across a lipid bilayer on the basis of the osmotic and fluoride ion-selective electrode (ISE) assays, during which an electrogenic anion transport mechanism is found operative, whereas no transmembrane transport activity was found with 2 and 3, despite the fact that 2 and 3 are also able to bind fluoride via the thiourea moieties. These results demonstrate that the encapsulation of an anionic guest within a cyclic host compound is key to enhancing the anion transport activity and selectivity. |
Databáze: | OpenAIRE |
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