Anion binding and transport with meso-alkyl substituted two-armed calix[4]pyrroles bearing urea and hydroxyl groups
Pamuła, M., Bulatov, E., Martínez-Crespo, L., Kiesilä, A., Naulapää, J., Kalenius, E., & Helttunen, K. (2023). Anion binding and transport with meso-alkyl substituted two-armed calix[4]pyrroles bearing urea and hydroxyl groups. Organic and Biomolecular Chemistry, 21(32), 6595-6603. https://doi.org/10.1039/d3ob00919j
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Organic and Biomolecular ChemistryAuthors
Date
2023Discipline
Nanoscience CenterOrgaaninen kemiaEpäorgaaninen kemiaEpäorgaaninen ja analyyttinen kemiaAnalyyttinen kemiaNanoscience CenterOrganic ChemistryInorganic ChemistryInorganic and Analytical ChemistryAnalytical ChemistryCopyright
© 2023 Royal Society of Chemistry (RSC)
Calix[4]pyrroles bearing hydroxyl (1) or urea (3) groups attached to the meso-positions with propyl linkers were synthesized as cis- and trans-isomers. The anion binding properties of cis-1 and cis-3 were screened with ion-mobility mass spectrometry, where cis-1 formed complexes with Cl−, Br− and H2PO4−, whereas cis-3 formed complexes with most of the investigated anions, including Cl−, Br−, I−, NO3−, ClO4−, OTf−, SCN− and PF6−. The structures of the chloride complexes were further elucidated with density functional theory calculations and a crystal structure obtained for cis-1. In solution, chloride and dihydrogenphosphate anion binding with cis-1 and cis-3 were compared using 1H NMR titrations. To assess the suitability of two-armed calix[4]pyrroles as anion transporters, chloride transport studies of cis-1, cis-3 and trans-3 were performed using large unilamellar vesicles. The results revealed that cis-3 had the highest activity among the investigated calix[4]pyrroles, which was related to the improved affinity and isolation of chloride inside the binding cavity of cis-3 in comparison to cis-1. The results indicate that appending calix[4]pyrroles with two hydrogen bonding arms is a feasible strategy to obtain anion transporters and receptors with high anion affinity.
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Royal Society of Chemistry (RSC)ISSN Search the Publication Forum
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https://converis.jyu.fi/converis/portal/detail/Publication/184073870
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Research Council of FinlandFunding program(s)
Research costs of Academy Research Fellow, AoF; Academy Research Fellow, AoFAdditional information about funding
We wish to thank Prof. Pablo Ballester for hosting KH for a research stage and the Research Support Area of ICIQ for data acquisition. Dr Laura Laverdure is sincerely thanked for consulting the computational part of this work. Academy of Finland is acknowledged for financial support (projects 309910, 314287, and 335685). LM-C acknowledges the Ministerio de Universidades (Spanish government) for the María Zambrano grant awarded under the Recovery, Transformation and Resilience Plan (NextGenerationEU). ...License
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