trifluoromethionine

Trifluoromethionine is a non-proteinogenic amino acid and a fluorinated analogue of methionine in which the methyl group of methionine is replaced by a trifluoromethyl group. It is classified as an organofluorine compound and belongs to the class of L-alpha-amino acids. Trifluoromethionine acts as an antimicrobial agent with demonstrated in vitro toxicity against anaerobic protozoan parasites such as Trichomonas vaginalis and certain bacterial strains expressing methionine gamma lyase (MGL). Its mechanism involves targeting enzymes like methionyl-tRNA synthetase (methionyl-tRNA ligase), methionine aminopeptidase, and particularly relies on the presence of MGL for its cytotoxic effects. Resistance can develop through downregulation or absence of MGL activity[5][7][8]. The compound has been used primarily in research settings to study protein engineering, enzyme mechanisms, and antimicrobial activity rather than as an approved pharmaceutical drug[1][2][5].

Other names

trifluoro-L-methionine(S)-2-amino-4-((trifluoromethyl)thio)butanoic acidL-homocysteine S-(trifluoromethyl)764-52-3