Towards DNA-encoded micellar chemistry: DNA-micelle association and environment sensitivity of catalysis

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dc.contributor.authorKlika Škopić, Mateja
dc.contributor.authorGramse, Christian
dc.contributor.authorOliva, Rosario
dc.contributor.authorPospich, Sabrina
dc.contributor.authorNeukirch, Laura
dc.contributor.authorManisegaran, Magiliny
dc.contributor.authorRaunser, Stefan
dc.contributor.authorWinter, Roland
dc.contributor.authorWeberskirch, Ralf
dc.contributor.authorBrunschweiger, Andreas
dc.date.accessioned2022-03-30T11:03:08Z
dc.date.available2022-03-30T11:03:08Z
dc.date.issued2021-05-12
dc.description.abstractThe development of DNA-compatible reaction methodologies is a central theme to advance DNA-encoded screening library technology. Recently, we were able to show that sulfonic acid-functionalized block copolymer micelles facilitated Brønsted acid-promoted reactions such as the Povarov reaction on DNA-coupled starting materials with minimal DNA degradation. Here, the impact of polymer composition on micelle shape, and reaction conversion was investigated. A dozen sulfonic acid-functionalized block copolymers of different molar mass and composition were prepared by RAFT polymerization and were tested in the Povarov reaction, removal of the Boc protective group, and the Biginelli reaction. The results showed trends in the polymer structure-micellar catalytic activity relationship. For instance, micelles composed of block copolymers with shorter acrylate ester chains formed smaller particles and tended to provide faster reaction kinetics. Moreover, fluorescence quenching experiments as well as circular dichroism spectroscopy showed that DNA-oligomer-conjugates, although highly water-soluble, accumulated very effectively in the micellar compartments, which is a prerequisite for carrying out a DNA-encoded reaction in the presence of polymer micelles.en
dc.identifier.urihttp://hdl.handle.net/2003/40838
dc.identifier.urihttp://dx.doi.org/10.17877/DE290R-22695
dc.language.isoende
dc.relation.ispartofseriesChemistry - a European journal;27(39)
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/
dc.subjectCopolymersen
dc.subjectDNA conjugatesen
dc.subjectHeterocycle synthesisen
dc.subjectMicellar catalysisen
dc.subjectPartitioningen
dc.subject.ddc570
dc.subject.ddc540
dc.titleTowards DNA-encoded micellar chemistry: DNA-micelle association and environment sensitivity of catalysisen
dc.typeTextde
dc.type.publicationtypearticlede
dcterms.accessRightsopen access
eldorado.secondarypublicationtruede
eldorado.secondarypublication.primarycitationM. Klika Škopić, C. Gramse, R. Oliva, S. Pospich, L. Neukirch, M. Manisegaran, S. Raunser, R. Winter, R. Weberskirch, A. Brunschweiger, Chem. Eur. J. 2021, 27, 10048.de
eldorado.secondarypublication.primaryidentifierhttps://doi.org/10.1002/chem.202100980de

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