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- Title
Genetic Encoding of Cyanopyridylalanine for In‐Cell Protein Macrocyclization by the Nitrile–Aminothiol Click Reaction.
- Authors
Abdelkader, Elwy H.; Qianzhu, Haocheng; George, Josemon; Frkic, Rebecca L.; Jackson, Colin J.; Nitsche, Christoph; Otting, Gottfried; Huber, Thomas
- Abstract
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.
- Subjects
AMINOACYL-tRNA synthetases; PROTEINS; AMINO acids; PEPTIDES
- Publication
Angewandte Chemie, 2022, Vol 134, Issue 13, p1
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202114154