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dc.contributor.authorTwum, Kwaku
dc.contributor.authorIraj Sadraei, Seyed
dc.contributor.authorFeder, Jordan
dc.contributor.authorTaimoory, S. Maryamdokht
dc.contributor.authorRissanen, Kari
dc.contributor.authorTrant, John F.
dc.contributor.authorBeyeh, Ngong Kodiah
dc.date.accessioned2022-02-28T09:38:57Z
dc.date.available2022-02-28T09:38:57Z
dc.date.issued2022
dc.identifier.citationTwum, K., Iraj Sadraei, S., Feder, J., Taimoory, S. M., Rissanen, K., Trant, J. F., & Beyeh, N. K. (2022). Sharing the salt bowl : counterion identity drives N-alkyl resorcinarene affinity for pyrophosphate in water. <i>Organic Chemistry Frontiers</i>, <i>9</i>(5), 1267-1275. <a href="https://doi.org/10.1039/D1QO01877A" target="_blank">https://doi.org/10.1039/D1QO01877A</a>
dc.identifier.otherCONVID_104377637
dc.identifier.urihttps://jyx.jyu.fi/handle/123456789/79986
dc.description.abstractN-Alkyl ammonium resorcinarene chloride receptors, NARX4, have been shown to act as high-sensitivity detectors of pyrophosphate (PPi), a biomarker of disease, in aqueous media through the chloride-to-PPi exchange [NAR(Cl)4 to NARPPi]. The nature of the anion of the macrocyclic NARX4 (X = Cl−, Br−, triflate OTf−) receptor greatly influences the PPi-affinity in aqueous media. The binding affinity for [NAR (Cl)4] is 3.61 × 105 M−1, while the NAR (Br)4 and NAR (OTf)4 show stronger binding of 5.30 × 105 M−1, and 6.10 × 105 M−1, respectively. The effects of upper rim ammonium cation, –N+H2R substituents (R = 3-hydroxypropyl, cyclohexyl, benzyl, or napththalen-1-ylmethyl), of the macrocyclic resorcinarene hosts have also been evaluated. The highest affinity was obtained using 3-hydroxypropyl groups due to the additional hydrogen bonds and the naphthyl upper-rim group that provides a larger hydrophobic surface area and favorable stacking interaction (i.e., π–π and CH–π). We note that two PPi molecules can bind to the more selective receptors through an additional interaction with the lower rim hydroxyls, making the resorcinarene a divalent binder. Comparing PPi with other phosphate anions (PO43−, AMP, ADP, and ATP) shows that the receptors are more selective for PPi due to the size and charge complementarity. Experimental (1H, 31P NMR, and isothermal titration calorimetry), and computational analyses support the reported trends for PPi selectivity even in highly competing aqueous media.en
dc.format.mimetypeapplication/pdf
dc.language.isoeng
dc.publisherRoyal Society of Chemistry (RSC)
dc.relation.ispartofseriesOrganic Chemistry Frontiers
dc.rightsCC BY 4.0
dc.titleSharing the salt bowl : counterion identity drives N-alkyl resorcinarene affinity for pyrophosphate in water
dc.typearticle
dc.identifier.urnURN:NBN:fi:jyu-202202281709
dc.contributor.laitosKemian laitosfi
dc.contributor.laitosDepartment of Chemistryen
dc.contributor.oppiaineOrgaaninen kemiafi
dc.contributor.oppiaineOrganic Chemistryen
dc.type.urihttp://purl.org/eprint/type/JournalArticle
dc.description.reviewstatuspeerReviewed
dc.format.pagerange1267-1275
dc.relation.issn2052-4110
dc.relation.numberinseries5
dc.relation.volume9
dc.type.versionpublishedVersion
dc.rights.copyright© 2022 the Partner Organisations
dc.rights.accesslevelopenAccessfi
dc.subject.ysobiomarkkerit
dc.subject.ysosupramolekulaarinen kemia
dc.subject.ysofosfaatit
dc.subject.ysoliuokset
dc.subject.ysokemialliset sidokset
dc.format.contentfulltext
jyx.subject.urihttp://www.yso.fi/onto/yso/p12288
jyx.subject.urihttp://www.yso.fi/onto/yso/p37759
jyx.subject.urihttp://www.yso.fi/onto/yso/p8696
jyx.subject.urihttp://www.yso.fi/onto/yso/p4335
jyx.subject.urihttp://www.yso.fi/onto/yso/p10130
dc.rights.urlhttps://creativecommons.org/licenses/by/4.0/
dc.relation.doi10.1039/D1QO01877A
jyx.fundinginformationThe authors gratefully acknowledge financial support from the Provost Graduate Research Scholarship (KT, JF), Oakland University, MI, USA, and the University of Windsor, ON, Canada. This work was made possible by the facilities of the Shared Hierarchical Academic Research Computing Network (SHARCNET: http://www.sharcnet.ca) and Compute/Calcul Canada. This work was funded in part by the Natural Sciences and Engineering Research Council of Canada (Grant # 2018-06338 to JFT), the Windsor Cancer Centre Foundation Seeds4Hope Seed Grant Funding Program (Grant # 2017-03 to JFT), and an Ontario Early Researcher Award (Grant # ER18-14-114 to JFT).


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