A Vitamin B₂ -Photocatalysed Approach to Methionine Analogues.

ABSTRACT: Access to new non-canonical amino acid residues is crucial for medicinal chemistry and chemical biology. Analogues of the amino acid methionine have been far less explored-despite their use in biochemistry, pharmacology and peptide bioconjugation. This is largely due to limited synthetic access. Herein, we exploit a new disconnection to access non-natural methionines through the development of a photochemical method for the radical α-C-H functionalization of sulfides with alkenes, in water, using inexpensive and commercially-available riboflavin (vitamin B₂ ) as a photocatalyst. Our photochemical conditions allow the two-step synthesis of novel methionine analogues-by radical addition to unsaturated amino acid derivatives-and the chemoselective modification of peptide side-chain

SUBMITTER: Knowles OJ 

PROVIDER: S-EPMC10100050 | biostudies-literature | 2022 Dec

REPOSITORIES: biostudies-literature