dc.contributor.author | Schischko, Alexandra | |
dc.contributor.author | Kaplaneris, Nikolaos | |
dc.contributor.author | Rogge, Torben | |
dc.contributor.author | Sirvinskaite, Giedre | |
dc.contributor.author | Son, Jongwoo | |
dc.contributor.author | Ackermann, Lutz | |
dc.date.accessioned | 2019-10-29T09:47:31Z | |
dc.date.available | 2019-10-29T09:47:31Z | |
dc.date.issued | 2019 | de |
dc.identifier.ISBN | 31391461 | |
dc.relation.ISSN | 2041-1723 | de |
dc.identifier.uri | http://resolver.sub.uni-goettingen.de/purl?gs-1/16571 | |
dc.description.abstract | Methods 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.iso | eng | de |
dc.relation | info:eu-repo/grantAgreement/EC/FP7/307535/EU//CATCHFUN | de |
dc.rights | openAccess | |
dc.rights.uri | https://creativecommons.org/licenses/by/4.0/ | |
dc.subject | C–H; peptide synthesis; alkylation | de |
dc.subject.ddc | 540 | |
dc.title | Late-stage peptide C–H alkylation for bioorthogonal C–H activation featuring solid phase peptide synthesis | de |
dc.type | journalArticle | de |
dc.identifier.doi | 10.1038/s41467-019-11395-3 | |
dc.type.version | publishedVersion | de |
dc.relation.eISSN | 2041-1723 | |
dc.bibliographicCitation.volume | 10 | de |
dc.bibliographicCitation.issue | 1 | de |
dc.type.subtype | journalArticle | |
dc.bibliographicCitation.articlenumber | 3553 | de |
dc.description.status | peerReviewed | de |
dc.bibliographicCitation.journal | Nature Communications | de |