{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,3]],"date-time":"2026-09-03T22:30:40Z","timestamp":1788474640218,"version":"build-2803163510"},"reference-count":59,"publisher":"Wiley","issue":"1","license":[{"start":{"date-parts":[[2025,12,12]],"date-time":"2025-12-12T00:00:00Z","timestamp":1765497600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2025,12,12]],"date-time":"2025-12-12T00:00:00Z","timestamp":1765497600000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemPlusChem"],"published-print":{"date-parts":[[2026,1]]},"abstract":"<jats:p>\n                    The rise of antifungal resistance threatens public health and agriculture. Iturin A, a cyclic lipopeptide produced by\n                    <jats:italic>Bacillus<\/jats:italic>\n                    species, is known for its antifungal activity against various pathogens. In this study, three novel trifluoromethylated analogues of iturin A were synthesised as potential\n                    <jats:sup>19<\/jats:sup>\n                    F NMR probes and to compare their bioactivity with the natural compound. Trifluoromethylation targeted the D\u2010tyrosine and iturinic acid residues, which are critical for antifungal activity. Fluorinated building blocks were prepared via oxidative radical trifluoromethylation for D\u2010tyrosine and, notably, via electrophilic trifluoromethylation combined with a chiral auxiliary\u2010based approach for the iturinic acid, marking the first synthesis of a terminally trifluoromethylated long\u2010chain \u03b2\u2010amino fatty acid. Peptide assembly was achieved through solid\u2010phase synthesis followed by on\u2010resin cyclisation, alongside a high\u2010yielding late\u2010stage aromatic trifluoromethylation method. Bioactivity assays revealed that the mono\u2010trifluoromethylated tyrosine analogue exhibited slight activity loss against\n                    <jats:italic>Candida albicans<\/jats:italic>\n                    and greater loss against\n                    <jats:italic>Fusarium graminearum<\/jats:italic>\n                    . The bis\u2010trifluoromethylated tyrosine analogue lost activity against both fungi, while the alkyl\u2010trifluoromethylated analogue retained full activity against\n                    <jats:italic>C. albicans<\/jats:italic>\n                    and showed a minor activity loss against\n                    <jats:italic>F. graminearum<\/jats:italic>\n                    . These analogues provide insights into site\u2010specific trifluoromethylation effects, can serve as valuable\n                    <jats:sup>19<\/jats:sup>\n                    F NMR probes, and can be a platform for further iturin A analogue development.\n                  <\/jats:p>","DOI":"10.1002\/cplu.202500590","type":"journal-article","created":{"date-parts":[[2025,12,13]],"date-time":"2025-12-13T00:40:18Z","timestamp":1765586418000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Synthesis of Trifluoromethylated Analogues of the Cyclic Lipopeptide Iturin A and Evaluation of their Antifungal Activity"],"prefix":"10.1002","volume":"91","author":[{"given":"Periklis","family":"Karamanis","sequence":"first","affiliation":[{"name":"UCD School of Chemistry University College Dublin  Dublin Ireland"},{"name":"BiOrbic Bioeconomy SFI Research Centre University College Dublin  Dublin 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