Rapid on-resin N-formylation of peptides as one-pot reaction

• Verfasst von: Kokollari, Agon [VerfasserIn]
• Verfasst von: Werner, Marius [VerfasserIn]
• Verfasst von: Lindner, Christina [VerfasserIn]
• Verfasst von: Pham, Truc Lam [VerfasserIn]
• Verfasst von: Thomas, Franziska [VerfasserIn]
• Titel: Rapid on-resin N-formylation of peptides as one-pot reaction
• Verf.angabe: Agon Kokollari, Marius Werner, Christina Lindner, Truc Lam Pham, and Franziska Thomas
• Ausgabe: Online version of record before inclusion in an issue
• E-Jahr: 2023
• Jahr: 11 September 2023
• Umfang: 6 S.
• Illustrationen: Illustrationen
• Fussnoten: Gesehen am 19.10.2023
• Titel Quelle: Enthalten in: ChemBioChem
• Ort Quelle: Weinheim : Wiley-VCH, 2000
• Jahr Quelle: 2023
• Band/Heft Quelle: (2023), Artikel-ID e202300571, Seite 1-6
• ISSN Quelle: 1439-7633
• DOI: doi:10.1002/cbic.202300571
• Datenträger: Online-Ressource
• Sprache: eng
• Bibliogr. Hinweis: Forschungsdaten: Kokollari, Agon, 2002 - : Rapid on-resin N-formylation of peptides as one-pot reaction [research data]
• Sach-SW: chemotactic peptides
• Sach-SW: late-stage formylation
• Sach-SW: post-translational modification
• Sach-SW: protein modifications
• Sach-SW: solid-phase synthesis
• K10plus-PPN: 186637415X

Abstract

N-formylation is a common pre- and post-translational modification of the N-terminus or the lysine side chain of peptides and proteins that plays a role in the initiation of immune responses, gene expression, or epigenetics. Despite its high biological relevance, protocols for the chemical N-formylation of synthetic peptides are scarce. The few available methods are elaborate in their execution and the yields are highly sequence-dependent. We present a rapid, easy-to-use one-pot procedure that runs at room temperature and can be used to formylate protected peptides at both the N-terminus and the lysine side chain on the resin in near-quantitative yields. Only insensitive, storage-stable standard chemicals - formic acid, acetic anhydride, pyridine and DMF - are used. Formylation works for both short and long peptides of up to 34 amino acids and over the spectrum of canonical amino acids.