132436-46-5Relevant articles and documents
Redox-based reagents for chemoselective methionine bioconjugation
Lin, Shixian,Yang, Xiaoyu,Jia, Shang,Weeks, Amy M.,Hornsby, Michael,Lee, Peter S.,Nichiporuk, Rita V.,Iavarone, Anthony T.,Wells, James A.,Toste, F. Dean,Chang, Christopher J.
, p. 597 - 602 (2017)
Cysteine can be specifically functionalized by a myriad of acid-base conjugation strategies for applications ranging from probing protein function to antibody-drug conjugates and proteomics. In contrast, selective ligation to the other sulfur-containing amino acid, methionine, has been precluded by its intrinsically weaker nucleophilicity. Here, we report a strategy for chemoselective methionine bioconjugation through redox reactivity, using oxaziridine-based reagents to achieve highly selective, rapid, and robust methionine labeling under a range of biocompatible reaction conditions. We highlight the broad utility of this conjugation method to enable precise addition of payloads to proteins, synthesis of antibody-drug conjugates, and identification of hyperreactive methionine residues in whole proteomes.
