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dc.contributor.authorPamuła, Małgorzata
dc.contributor.authorBulatov, Evgeny
dc.contributor.authorMartínez-Crespo, Luis
dc.contributor.authorKiesilä, Anniina
dc.contributor.authorNaulapää, Julia
dc.contributor.authorKalenius, Elina
dc.contributor.authorHelttunen, Kaisa
dc.date.accessioned2023-09-01T10:54:39Z
dc.date.available2023-09-01T10:54:39Z
dc.date.issued2023
dc.identifier.citationPamuła, 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. <i>Organic and Biomolecular Chemistry</i>, <i>21</i>(32), 6595-6603. <a href="https://doi.org/10.1039/d3ob00919j" target="_blank">https://doi.org/10.1039/d3ob00919j</a>
dc.identifier.otherCONVID_184073870
dc.identifier.urihttps://jyx.jyu.fi/handle/123456789/88852
dc.description.abstractCalix[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.en
dc.format.mimetypeapplication/pdf
dc.language.isoeng
dc.publisherRoyal Society of Chemistry (RSC)
dc.relation.ispartofseriesOrganic and Biomolecular Chemistry
dc.rightsCC BY 3.0
dc.titleAnion binding and transport with meso-alkyl substituted two-armed calix[4]pyrroles bearing urea and hydroxyl groups
dc.typearticle
dc.identifier.urnURN:NBN:fi:jyu-202309014886
dc.contributor.laitosKemian laitosfi
dc.contributor.laitosDepartment of Chemistryen
dc.contributor.oppiaineNanoscience Centerfi
dc.contributor.oppiaineOrgaaninen kemiafi
dc.contributor.oppiaineEpäorgaaninen kemiafi
dc.contributor.oppiaineEpäorgaaninen ja analyyttinen kemiafi
dc.contributor.oppiaineAnalyyttinen kemiafi
dc.contributor.oppiaineNanoscience Centeren
dc.contributor.oppiaineOrganic Chemistryen
dc.contributor.oppiaineInorganic Chemistryen
dc.contributor.oppiaineInorganic and Analytical Chemistryen
dc.contributor.oppiaineAnalytical Chemistryen
dc.type.urihttp://purl.org/eprint/type/JournalArticle
dc.type.coarhttp://purl.org/coar/resource_type/c_2df8fbb1
dc.description.reviewstatuspeerReviewed
dc.format.pagerange6595-6603
dc.relation.issn1477-0520
dc.relation.numberinseries32
dc.relation.volume21
dc.type.versionpublishedVersion
dc.rights.copyright© 2023 Royal Society of Chemistry (RSC)
dc.rights.accesslevelopenAccessfi
dc.relation.grantnumber314287
dc.relation.grantnumber309910
dc.relation.grantnumber335685
dc.subject.ysoanionit
dc.subject.ysositoutuminen (kemia)
dc.subject.ysomassaspektrometria
dc.format.contentfulltext
jyx.subject.urihttp://www.yso.fi/onto/yso/p27229
jyx.subject.urihttp://www.yso.fi/onto/yso/p39500
jyx.subject.urihttp://www.yso.fi/onto/yso/p10755
dc.rights.urlhttps://creativecommons.org/licenses/by/3.0/
dc.relation.doi10.1039/d3ob00919j
dc.relation.funderResearch Council of Finlanden
dc.relation.funderResearch Council of Finlanden
dc.relation.funderResearch Council of Finlanden
dc.relation.funderSuomen Akatemiafi
dc.relation.funderSuomen Akatemiafi
dc.relation.funderSuomen Akatemiafi
jyx.fundingprogramResearch costs of Academy Research Fellow, AoFen
jyx.fundingprogramAcademy Research Fellow, AoFen
jyx.fundingprogramResearch costs of Academy Research Fellow, AoFen
jyx.fundingprogramAkatemiatutkijan tutkimuskulut, SAfi
jyx.fundingprogramAkatemiatutkija, SAfi
jyx.fundingprogramAkatemiatutkijan tutkimuskulut, SAfi
jyx.fundinginformationWe 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).
dc.type.okmA1


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