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dc.contributor.authorMungalpara, Disha
dc.contributor.authorValkonen, Arto
dc.contributor.authorRissanen, Kari
dc.contributor.authorKubik, Stefan
dc.date.accessioned2017-10-02T10:03:22Z
dc.date.available2017-10-02T10:03:22Z
dc.date.issued2017
dc.identifier.citationMungalpara, D., Valkonen, A., Rissanen, K., & Kubik, S. (2017). Efficient stabilisation of a dihydrogenphosphate tetramer and a dihydrogenpyrophosphate dimer by a cyclic pseudopeptide containing 1,4-disubstituted 1,2,3-triazole moieties. <em>Chemical Science</em>, 8 (9), 6005-6013. <a href="https://doi.org/10.1039/C7SC02700A">doi:10.1039/C7SC02700A</a>
dc.identifier.otherTUTKAID_74950
dc.identifier.urihttps://jyx.jyu.fi/handle/123456789/55492
dc.description.abstractA cyclic pseudooctapeptide 2 is described containing 1,4-disubstituted 1,2,3-triazole moieties. This compound features eight converging hydrogen bond donors along the ring, namely four amide NH and four triazole CH groups, which enable 2 to engage in interactions with anions. While fully deprotonated sulfate anions exhibit only moderate affinity for 2, protonated anions such as dihydrogenpyrophosphate and dihydrogenphosphate anions are strongly bound. Complexation of the phosphate-derived anions involves sandwiching of a dihydrogenpyrophosphate dimer or a dihydrogenphosphate tetramer between two pseudopeptide rings. X-ray crystallography provided structural information, while 1 H NMR spectroscopy, mass spectrometry, and isothermal titration calorimetry demonstrated that these complexes are stable in solution (2.5 vol% water/ DMSO) and can even be transferred without decomposition into the gas phase. The observed high thermodynamic stabilities are attributed to the mutual reinforcement of the interactions between the individual complex components, namely, hydrogen-bonding between the anions, multiple hydrogen bonding interactions between the anion aggregates and the triazole CH and NH hydrogen bond donors of 2, and potential dispersive interactions between the closely arranged pseudopeptide rings. Pseudopeptide 2 thus represents a promising lead for the construction of phosphate receptors, whose binding selectivity makes use of the unique ability of certain anions to assemble into higher aggregates.
dc.language.isoeng
dc.publisherRoyal Society of Chemistry
dc.relation.ispartofseriesChemical Science
dc.subject.otherorgaaniset yhdisteet
dc.subject.otherfosfaatit
dc.subject.otheroligomeeri
dc.subject.otherpseudopeptides
dc.subject.otherphosphate oligomers
dc.subject.otherstabilisation
dc.titleEfficient stabilisation of a dihydrogenphosphate tetramer and a dihydrogenpyrophosphate dimer by a cyclic pseudopeptide containing 1,4-disubstituted 1,2,3-triazole moieties
dc.typearticle
dc.identifier.urnURN:NBN:fi:jyu-201709213791
dc.contributor.laitosKemian laitosfi
dc.contributor.laitosDepartment of Chemistryen
dc.contributor.oppiaineOrgaaninen kemia
dc.type.urihttp://purl.org/eprint/type/JournalArticle
dc.date.updated2017-09-21T12:15:16Z
dc.type.coarjournal article
dc.description.reviewstatuspeerReviewed
dc.format.pagerange6005-6013
dc.relation.issn2041-6520
dc.relation.volume8
dc.type.versionpublishedVersion
dc.rights.copyright© the Authors, 2017. This is an open access article distributed under the terms of a Creative Commons License.
dc.rights.accesslevelopenAccessfi
dc.rights.urlhttps://creativecommons.org/licenses/by-nc/3.0/
dc.relation.doi10.1039/C7SC02700A


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© the Authors, 2017. This is an open access article distributed under the terms of a Creative Commons License.
Except where otherwise noted, this item's license is described as © the Authors, 2017. This is an open access article distributed under the terms of a Creative Commons License.