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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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Main Authors: Thomas, Franziska (Author) , Brinkhofer, Julian (Author) , Werner, Marius (Author) , Kokollari, Agon (Author) , Pan, Shih-Yu (Author) , Klein, Christian D. (Author) , Pham, Truc Lam (Author)
Format: Database Research Data
Language:English
Published: Heidelberg Universität 2026-07-06
DOI:10.11588/DATA/WCJFQB
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Forschungsdaten
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Online Access: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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Author Notes:Franziska Thomas, Julian Brinkhofer, Marius Werner, Agon Kokollari, Shih-Yu Pan, Christian Klein, Truc Lam Pham
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Summary: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.
Item Description: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'
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Physical Description:Online Resource
DOI:10.11588/DATA/WCJFQB

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