Late-stage amination of peptides on the solid phase [data]
Late-stage peptide modification is a powerful tool for rapidly generating a library of peptide mimetics, for example, for drug discovery or catalyst development. While late-stage modifications exist for many types of structural features, methods for introducing amines into peptides via a late-stage...
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| Autori principali: | , , , , , , |
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| Natura: | Database Research Data |
| Lingua: | inglese |
| Pubblicazione: |
Heidelberg
Universität
2026-07-06
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| DOI: | 10.11588/DATA/WCJFQB |
| Soggetti: | |
| Accesso online: | Verlag, kostenfrei, Volltext: https://doi.org/10.11588/DATA/WCJFQB Verlag, kostenfrei, Volltext: https://heidata.uni-heidelberg.de/dataset.xhtml?persistentId=doi:10.11588/DATA/WCJFQB 
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| Note sull'autore: | Franziska Thomas, Julian Brinkhofer, Marius Werner, Agon Kokollari, Shih-Yu Pan, Christian Klein, Truc Lam Pham |
| Riassunto: | Late-stage peptide modification is a powerful tool for rapidly generating a library of peptide mimetics, for example, for drug discovery or catalyst development. While late-stage modifications exist for many types of structural features, methods for introducing amines into peptides via a late-stage approach are rare, despite their enormous potential for the development of peptide therapeutics. Here we present a protocol for introducing amines into peptides by our established on-resin iodination-substitution approach. Our method is compatible with a wide variety of amines, including primary and secondary amines, anilines, and other heteroaromatic N-nucleophiles mostly giving good to excellent yields. We introduce amines that are pharmacologically relevant as well as those that can impart catalytic or metal-binding properties into the peptide of interest. As a proof-of-concept study, we introduce the metal ligand tris(2-aminoethyl)amine (tren) into a tryptophan zipper scaffold using our late-stage amination approach to explore metal-induced stapling. Indeed, metal complexation via the tren ligand resulted in a thermal stabilization of more than 30 K in one of our tryptophan zipper designs. |
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| Descrizione del documento: | Gefördert durch: Fonds der Chemischen Industrie: Kekulé Fellowship; Ministerium für Wissenschaft, Forschung und Kunst Baden-Württemberg: ExU 6.1.16.3; Bundesministerium für Bildung und Forschung: ExU 6.1.16.3; Deutsche Forschungsgemeinschaft: ExU 6.1.16.3; Deutsche Forschungsgemeinschaft: EXC-2082/1-390761711; Bundesministerium für Bildung und Forschnung: Max Planck School 'Matter to Life'; Max-Planck-Gesellschaft: Max Planck School 'Matter to Life' Gesehen am 01.07.2026 |
| Descrizione fisica: | Online Resource |
| DOI: | 10.11588/DATA/WCJFQB |