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Transmembrane Fluoride Transport by a Cyclic Azapeptide With Two β-Turns
- Source :
- Frontiers in Chemistry, Vol 8 (2021), Frontiers in Chemistry
- Publication Year :
- 2021
- Publisher :
- Frontiers Media S.A., 2021.
-
Abstract
- 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.
- Subjects :
- 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
Subjects
Details
- Language :
- English
- ISSN :
- 22962646
- Volume :
- 8
- Database :
- OpenAIRE
- Journal :
- Frontiers in Chemistry
- Accession number :
- edsair.doi.dedup.....75c1108d5da98bc9eaa2a2df81d72f75
- Full Text :
- https://doi.org/10.3389/fchem.2020.621323/full