Synthesis of Trifluoromethylated Analogues of the Cyclic Lipopeptide Iturin A and Evaluation of their Antifungal Activity.

ABSTRACT: The rise of antifungal resistance threatens public health and agriculture. Iturin A, a cyclic lipopeptide produced by Bacillus species, is known for its antifungal activity against various pathogens. In this study, three novel trifluoromethylated analogues of iturin A were synthesised as potential ¹⁹F NMR probes and to compare their bioactivity with the natural compound. Trifluoromethylation targeted the D-tyrosine and iturinic acid residues, which are critical for antifungal activity. Fluorinated building blocks were prepared via oxidative radical trifluoromethylation for D-tyrosine and, notably, via electrophilic trifluoromethylation combined with a chiral auxiliary-based approach for the iturinic acid, marking the first synthesis of a terminally trifluoromethylated long-chain

SUBMITTER: Karamanis P 

PROVIDER: S-EPMC12777510 | biostudies-literature | 2026 Jan

REPOSITORIES: biostudies-literature