Rapid On-Resin N-Formylation of Peptides as One-Pot Reaction [Research Data]

DOI

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.

Identifier
DOI https://doi.org/10.11588/data/00RULE
Related Identifier https://doi.org/10.1002/cbic.202300571
Metadata Access https://heidata.uni-heidelberg.de/oai?verb=GetRecord&metadataPrefix=oai_datacite&identifier=doi:10.11588/data/00RULE
Provenance
Creator Kokollari, Agon ORCID logo; Werner, Marius ORCID logo; Lindner, Christina ORCID logo; Pham, Truc Lam ORCID logo; Thomas, Franziska ORCID logo
Publisher heiDATA
Contributor Thomas, Franziska; Pham, Truc Lam
Publication Year 2024
Funding Reference Deutsche Forschungsgemeinschaft (DFG) 414261058, 2082/1–390761711 (3DMM2O) ; Fonds der Chemischen Industrie Kekulé Fellowship (T.L.P)
Rights CC BY 4.0; info:eu-repo/semantics/openAccess; http://creativecommons.org/licenses/by/4.0
OpenAccess true
Contact Thomas, Franziska (Heidelberg University); Pham, Truc Lam (Heidelberg University)
Representation
Resource Type Dataset
Format application/zip; application/vnd.openxmlformats-officedocument.wordprocessingml.document; application/pdf
Size 2946634; 11856573; 19753; 114281
Version 1.3
Discipline Chemistry; Natural Sciences