Annulative Editing of Peptide Side Chains: N-Pyridination of Lysine via Chichibabin Pyridine Synthesis in Hexafluoroisopropanol
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S Cai, C Wu, Z Zhang, X Chu, X Sun, S Jiang…
Organic …, 2025
ACS Publications
Modifying the lysine side chain through N-heteroaryl annulation offers a unique opportunity to tailor or edit the structure and properties of the parent peptides. Here, we report two new applications of the Chichibabin pyridine synthesis for lysine-specific peptide modification under mild conditions, employing two distinct classes of aldehyde reagents. Reactions with 2-arylacetaldehydes afforded symmetrical 3, 5-diarylpyridinium products via an abnormal Chichibabin pathway, whereas reactions with 2-hydroxyacetaldehyde yielded …
