DFT-Guided Discovery of Ethynyl-Triazolyl-Phosphinates as Modular Electrophiles for Chemoselective Cysteine Bioconjugation and Profiling

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dc.contributor.authorStieger, Christian E.ko
dc.contributor.authorPark, Yerinko
dc.contributor.authorde Geus, Mark A. R.ko
dc.contributor.authorKim, Dongjuko
dc.contributor.authorHuhn, Christianeko
dc.contributor.authorSlenczka, J. Sophiako
dc.contributor.authorOchtrop, Philippko
dc.contributor.authorMuechler, Judith M.ko
dc.contributor.authorSuessmuth, Roderich D.ko
dc.contributor.authorBroichhagen, Johannesko
dc.contributor.authorBaik, Mu-Hyunko
dc.contributor.authorHackenberger, Christian P. R.ko
dc.date.accessioned2022-10-18T02:01:17Z-
dc.date.available2022-10-18T02:01:17Z-
dc.date.created2022-08-29-
dc.date.created2022-08-29-
dc.date.created2022-08-29-
dc.date.issued2022-10-
dc.identifier.citationANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.61, no.41-
dc.identifier.issn1433-7851-
dc.identifier.urihttp://hdl.handle.net/10203/299009-
dc.description.abstractWe report the density functional theory (DFT) guided discovery of ethynyl-triazolyl-phosphinates (ETPs) as a new class of electrophilic warheads for cysteine selective bioconjugation. By using Cu-I-catalysed azide alkyne cycloaddition (CuAAC) in aqueous buffer, we were able to access a variety of functional electrophilic building blocks, including proteins, from diethynyl-phosphinate. ETP-reagents were used to obtain fluorescent peptide-conjugates for receptor labelling on live cells and a stable and a biologically active antibody-drug-conjugate. Moreover, we were able to incorporate ETP-electrophiles into an azide-containing ubiquitin under native conditions and demonstrate their potential in protein-protein conjugation. Finally, we showcase the excellent cysteine-selectivity of this new class of electrophile in mass spectrometry based, proteome-wide cysteine profiling, underscoring the applicability in homogeneous bioconjugation strategies to connect two complex biomolecules.-
dc.languageEnglish-
dc.publisherWILEY-V C H VERLAG GMBH-
dc.titleDFT-Guided Discovery of Ethynyl-Triazolyl-Phosphinates as Modular Electrophiles for Chemoselective Cysteine Bioconjugation and Profiling-
dc.typeArticle-
dc.identifier.wosid000842511800001-
dc.identifier.scopusid2-s2.0-85136477693-
dc.type.rimsART-
dc.citation.volume61-
dc.citation.issue41-
dc.citation.publicationnameANGEWANDTE CHEMIE-INTERNATIONAL EDITION-
dc.identifier.doi10.1002/anie.202205348-
dc.contributor.localauthorBaik, Mu-Hyun-
dc.contributor.nonIdAuthorStieger, Christian E.-
dc.contributor.nonIdAuthorde Geus, Mark A. R.-
dc.contributor.nonIdAuthorHuhn, Christiane-
dc.contributor.nonIdAuthorSlenczka, J. Sophia-
dc.contributor.nonIdAuthorOchtrop, Philipp-
dc.contributor.nonIdAuthorMuechler, Judith M.-
dc.contributor.nonIdAuthorSuessmuth, Roderich D.-
dc.contributor.nonIdAuthorBroichhagen, Johannes-
dc.contributor.nonIdAuthorHackenberger, Christian P. R.-
dc.description.isOpenAccessN-
dc.type.journalArticleArticle-
dc.subject.keywordAuthorAntibody-Drug-Conjugates-
dc.subject.keywordAuthorBioconjugation-
dc.subject.keywordAuthorCysteine Profiling-
dc.subject.keywordAuthorProtein-Based Electrophiles-
dc.subject.keywordAuthorProtein-Protein Conjugation-
dc.subject.keywordPlusMOLECULAR-ORBITAL THEORY-
dc.subject.keywordPlusNUCLEOPHILICITY-
dc.subject.keywordPlusPK(A)-
dc.subject.keywordPlusCONJUGATION-
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