Late-stage functionalisation of peptides on the solid phase by an iodination-substitution approach

• Verfasst von: Werner, Marius [VerfasserIn]
• Verfasst von: Pampel, Julius [VerfasserIn]
• Verfasst von: Pham, Truc Lam [VerfasserIn]
• Verfasst von: Thomas, Franziska [VerfasserIn]
• Titel: Late-stage functionalisation of peptides on the solid phase by an iodination-substitution approach
• Verf.angabe: Marius Werner, Julius Pampel, Truc Lam Pham, and Franziska Thomas
• E-Jahr: 2022
• Jahr: September 6, 2022
• Umfang: 7 S.
• Fussnoten: Online veröffentlicht am 14. Juni 2022 ; Gesehen am 19.12.2022
• Titel Quelle: Enthalten in: Chemistry - a European journal
• Ort Quelle: Weinheim : Wiley-VCH, 1995
• Jahr Quelle: 2022
• Band/Heft Quelle: 28(2022), 50, Artikel-ID e202201339, Seite 1-7
• ISSN Quelle: 1521-3765
• DOI: doi:10.1002/chem.202201339
• Datenträger: Online-Ressource
• Sprache: eng
• Bibliogr. Hinweis: Forschungsdaten: Werner, Marius, 1998 - : Late-stage functionalisation of peptides on the solid phase by an iodination-substitution approach [research data]
• Sach-SW: biosensors
• Sach-SW: late-stage functionalisation
• Sach-SW: peptides
• Sach-SW: solid-phase synthesis
• Sach-SW: WW domains
• K10plus-PPN: 1827897821
• K10plus-PPN:
  Universitätsbibliothek
• Lokale URL UB: Zum Volltext

Abstract

The functionalisation of peptides at a late synthesis stage holds great potential, for example, for the synthesis of peptide pharmaceuticals, fluorescent biosensors or peptidomimetics. Here we describe an on-resin iodination-substitution reaction sequence on homoserine that is also suitable for peptide modification in a combinatorial format. The reaction sequence is accessible to a wide range of sulfur nucleophiles with various functional groups including boronic acids, hydroxy groups or aromatic amines. In this way, methionine-like thioethers or thioesters and thiosulfonates are accessible. Next to sulfur nucleophiles, selenols, pyridines and carboxylic acids were successfully used as nucleophiles, whereas phenols did not react. The late-stage iodination-substitution approach is not only applicable to short peptides but also to the more complex 34-amino-acid WW domains. We applied this strategy to introduce 7-mercapto-4-methylcoumarin into a switchable ZnII responsive WW domain to design an iFRET-based ZnII sensor.