7r6o

Publication Abstract from PubMed

Cyanopyridylalanines are non-canonical amino acids that react with aminothiol compounds under physiological conditions in a biocompatible manner without requiring added catalyst. Here we present newly developed aminoacyl-tRNA synthetases for genetic encoding of meta- and para-cyanopyridylalanine to enable the site-specific attachment of a wide range of different functionalities. The outstanding utility of the cyanopyridine moiety is demonstrated by examples of i) post-translational functionalization of proteins, ii) in-cell macrocyclization of peptides and proteins, and iii) protein stapling. The biocompatible nature of the protein ligation chemistry enabled by the cyanopyridylalanine amino acid opens a new path to specific in vivo protein modifications in complex biological environments.

Genetic Encoding of Cyanopyridylalanine for In-Cell Protein Macrocyclization by the Nitrile-Aminothiol Click Reaction.,Abdelkader EH, Qianzhu H, George J, Frkic RL, Jackson CJ, Nitsche C, Otting G, Huber T Angew Chem Int Ed Engl. 2022 Jan 31:e202114154. doi: 10.1002/anie.202114154. PMID:35102680^[1]

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.