Rapid On-Resin N-Formylation of Peptides as One-Pot Reaction |
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Authors: | Agon Kokollari Marius Werner Christina Lindner Truc Lam Pham Prof. Dr. Franziska Thomas |
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Affiliation: | Institute of Organic Chemistry, Heidelberg University, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany |
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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. |
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Keywords: | chemotactic peptides late-stage formylation post-translational modification protein modifications solid-phase synthesis |
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