dc.contributor.author | Suut-Tuule, Elina | |
dc.contributor.author | Jarg, Tatsiana | |
dc.contributor.author | Tikker, Priit | |
dc.contributor.author | Lootus, Ketren-Marlein | |
dc.contributor.author | Martõnova, Jevgenija | |
dc.contributor.author | Reitalu, Rauno | |
dc.contributor.author | Ustrnul, Lukas | |
dc.contributor.author | Ward, Jas S. | |
dc.contributor.author | Rjabovs, Vitalijs | |
dc.contributor.author | Shubin, Kirill | |
dc.contributor.author | Nallaparaju, Jagadeesh V. | |
dc.contributor.author | Vendelin, Marko | |
dc.contributor.author | Preis, Sergei | |
dc.contributor.author | Öeren, Mario | |
dc.contributor.author | Rissanen, Kari | |
dc.contributor.author | Kananovich, Dzmitry | |
dc.contributor.author | Aav, Riina | |
dc.date.accessioned | 2024-09-20T04:46:06Z | |
dc.date.available | 2024-09-20T04:46:06Z | |
dc.date.issued | 2024 | |
dc.identifier.citation | Suut-Tuule, E., Jarg, T., Tikker, P., Lootus, K.-M., Martõnova, J., Reitalu, R., Ustrnul, L., Ward, J. S., Rjabovs, V., Shubin, K., Nallaparaju, J. V., Vendelin, M., Preis, S., Öeren, M., Rissanen, K., Kananovich, D., & Aav, R. (2024). Mechanochemically driven covalent self-assembly of a chiral mono-biotinylated hemicucurbit[8]uril. <i>Cell Reports Physical Science</i>, <i>5</i>(9), Article 102161. <a href="https://doi.org/10.1016/j.xcrp.2024.102161" target="_blank">https://doi.org/10.1016/j.xcrp.2024.102161</a> | |
dc.identifier.other | CONVID_243079025 | |
dc.identifier.uri | https://jyx.jyu.fi/handle/123456789/97106 | |
dc.description.abstract | Solution-based synthesis of complex molecules with high efficiency leverages supramolecular control over covalent bond formation. Herein, we present the mechanosynthesis of chiral mono-biotinylated hemicucurbit[8]urils (mixHC[8]s) via the condensation of D-biotin, (R,R)- or (S,S)-cyclohexa-1,2-diylurea, and paraformaldehyde. The selectivity of self-assembly is enhanced through mechanochemistry and by fostering non-covalent interactions, achieved by eliminating solvents and conducting the reaction in the solid state. Rigorous analysis of intermediates reveals key processes and chemical parameters influencing dynamic covalent chemistry. The library of ca. 50,000 theoretically predicted intermediates and products leads to covalent self-assembly of chiral hemicucurbiturils. Mechanochemically prepared diastereomeric (−)- and (+)-mixHC[8]s are suitable for anion binding and derivatization. Immobilization of the macrocycles on aminated silica produces a functional material capable of selective capture of anions, as demonstrated by efficient perchlorate removal from a spiked mineral matrix. | en |
dc.format.mimetype | application/pdf | |
dc.language.iso | eng | |
dc.publisher | Elsevier | |
dc.relation.ispartofseries | Cell Reports Physical Science | |
dc.rights | CC BY-NC-ND 4.0 | |
dc.subject.other | mechanochemistry | |
dc.subject.other | covalent self-assembly in solid state | |
dc.subject.other | dynamic covalent chemistry | |
dc.subject.other | hemicucurbituril | |
dc.subject.other | macrocycle | |
dc.subject.other | mechanistic study | |
dc.subject.other | anion binding | |
dc.subject.other | functionalized silica | |
dc.subject.other | perchlorate removal | |
dc.subject.other | solid-phase extraction | |
dc.title | Mechanochemically driven covalent self-assembly of a chiral mono-biotinylated hemicucurbit[8]uril | |
dc.type | article | |
dc.identifier.urn | URN:NBN:fi:jyu-202409205983 | |
dc.contributor.laitos | Kemian laitos | fi |
dc.contributor.laitos | Department of Chemistry | en |
dc.type.uri | http://purl.org/eprint/type/JournalArticle | |
dc.type.coar | http://purl.org/coar/resource_type/c_2df8fbb1 | |
dc.description.reviewstatus | peerReviewed | |
dc.relation.issn | 2666-3864 | |
dc.relation.numberinseries | 9 | |
dc.relation.volume | 5 | |
dc.type.version | publishedVersion | |
dc.rights.copyright | © 2024 The Author(s). Published by Elsevier Inc. | |
dc.rights.accesslevel | openAccess | fi |
dc.relation.grantnumber | 828779 | |
dc.relation.grantnumber | 828779 | |
dc.relation.projectid | info:eu-repo/grantAgreement/EC/H2020/828779/EU//INITIO | |
dc.subject.yso | sitoutuminen (kemia) | |
dc.subject.yso | piidioksidi | |
dc.subject.yso | anionit | |
dc.format.content | fulltext | |
jyx.subject.uri | http://www.yso.fi/onto/yso/p39500 | |
jyx.subject.uri | http://www.yso.fi/onto/yso/p5698 | |
jyx.subject.uri | http://www.yso.fi/onto/yso/p27229 | |
dc.rights.url | https://creativecommons.org/licenses/by-nc-nd/4.0/ | |
dc.relation.doi | 10.1016/j.xcrp.2024.102161 | |
dc.relation.funder | European Commission | en |
dc.relation.funder | Euroopan komissio | fi |
jyx.fundingprogram | FET Future and Emerging Technologies, H2020 | en |
jyx.fundingprogram | FET Future and Emerging Technologies, H2020 | fi |
jyx.fundinginformation | The authors would like to thank Jasper Adamson and Indrek Reile for input on the NMR analysis. The research by R.A., L.U., D.K., J.S.W., and K.R. was funded by the European Union’s H2020- FETOPEN grant 828779 (INITIO). E.S.-T., T.J., K.-M.L., J.V.N., J.M., R.R., and M.O. were financed by Estonian Research Council grants PRG399 and PRG2169. R.A. was funded by the Ministry of Education and Research through Centre of Excellence in Circular Economy for Strategic Mineral and Carbon Resources (01.01.2024–31.12.2030, TK228). The authors also acknowledge COST Action CA18112 “Mechanochemistry for Sustainable Industry” for supporting research in mechanochemistry. | |
dc.type.okm | A1 | |