Demethylative Alkylation of Methionine Residue by Employing the Sulfonium as the Key Intermediate

Org Lett. 2021 Nov 5;23(21):8543-8548. doi: 10.1021/acs.orglett.1c03241. Epub 2021 Oct 20.

Abstract

Methionine (Met) offers a valuable handle to achieve peptide chemical modification owing to its unique thioether functional group. In contrast with cysteine, the site-selective functionalization of the hydrophobic and redox-sensitive thioether motif on peptides is still challenging, and strategies for diversification on the Met residue are rarely disclosed. Herein we report a transition-metal-free and redox-neutral approach for Met diversification with substrate diversity, which could be applied to synthesize cyclic peptides.

Publication types

  • Research Support, Non-U.S. Gov't