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Late-stage peptide C–H alkylation for bioorthogonal C–H activation featuring solid phase peptide synthesis

dc.contributor.authorSchischko, Alexandra
dc.contributor.authorKaplaneris, Nikolaos
dc.contributor.authorRogge, Torben
dc.contributor.authorSirvinskaite, Giedre
dc.contributor.authorSon, Jongwoo
dc.contributor.authorAckermann, Lutz
dc.date.accessioned2019-10-29T09:47:31Z
dc.date.available2019-10-29T09:47:31Z
dc.date.issued2019de
dc.identifier.ISBN31391461
dc.relation.ISSN2041-1723de
dc.identifier.urihttp://resolver.sub.uni-goettingen.de/purl?gs-1/16571
dc.description.abstractMethods for the late-stage diversification of structurally complex peptides hold enormous potential for advances in drug discovery, agrochemistry and pharmaceutical industries. While C-H arylations emerged for peptide modifications, they are largely limited to highly reactive, expensive and/or toxic reagents, such as silver(I) salts, in superstoichiometric quantities. In sharp contrast, we herein establish the ruthenium(II)-catalyzed C-H alkylation on structurally complex peptides. The additive-free ruthenium(II)carboxylate C-H activation manifold is characterized by ample substrate scope, racemization-free conditions and the chemo-selective tolerance of otherwise reactive functional groups, such as electrophilic ketone, bromo, ester, amide and nitro substituents. Mechanistic studies by experiment and computation feature an acid-enabled C-H ruthenation, along with a notable protodemetalation step. The transformative peptide C-H activation regime sets the stage for peptide ligation in solution and proves viable in a bioorthogonal fashion for C-H alkylations on user-friendly supports by means of solid phase peptide syntheses.de
dc.language.isoengde
dc.relationinfo:eu-repo/grantAgreement/EC/FP7/307535/EU//CATCHFUNde
dc.rightsopenAccess
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/
dc.subjectC–H; peptide synthesis; alkylationde
dc.subject.ddc540
dc.titleLate-stage peptide C–H alkylation for bioorthogonal C–H activation featuring solid phase peptide synthesisde
dc.typejournalArticlede
dc.identifier.doi10.1038/s41467-019-11395-3
dc.type.versionpublishedVersionde
dc.relation.eISSN2041-1723
dc.bibliographicCitation.volume10de
dc.bibliographicCitation.issue1de
dc.type.subtypejournalArticle
dc.bibliographicCitation.articlenumber3553de
dc.description.statuspeerReviewedde
dc.bibliographicCitation.journalNature Communicationsde


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