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To allow the study of unsaturated free fatty acids in live cells, we here report the use of sterculic acid, a 1,2\u2010cyclopropene\u2010containing oleic acid analogue, as a bioorthogonal probe. We show that this lipid can be readily taken up by dendritic cells without toxic side effects, and that it can subsequently be visualised using an inverse electron\u2010demand Diels\u2013Alder reaction with quenched tetrazine\u2010fluorophore conjugates. In addition, the lipid can be used to identify changes in protein oleoylation after immune cell activation. Finally, this reaction can be integrated into a multiplexed bioorthogonal reaction workflow by combining it with two sequential copper\u2010catalysed Huisgen ligation reactions. This allows for the study of multiple biomolecules in the cell simultaneously by multimodal confocal imaging.<\/jats:p>","DOI":"10.1002\/anie.202207640","type":"journal-article","created":{"date-parts":[[2022,7,15]],"date-time":"2022-07-15T08:34:50Z","timestamp":1657874090000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":31,"title":["Live\u2010Cell Imaging of Sterculic Acid\u2014a Naturally Occurring 1,2\u2010Cyclopropene Fatty Acid\u2014by Bioorthogonal Reaction with Turn\u2010On Tetrazine\u2010Fluorophore Conjugates**"],"prefix":"10.1002","volume":"61","author":[{"given":"Kristine","family":"Bertheussen","sequence":"first","affiliation":[{"name":"Department of Bio-Organic Synthesis Leiden Institute of Chemistry Leiden University  Einsteinweg 55 2333 CC Leiden The Netherlands"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Merel","family":"van de Plassche","sequence":"additional","affiliation":[{"name":"Department of Bio-Organic Synthesis Leiden Institute of Chemistry Leiden University  Einsteinweg 55 2333 CC Leiden The Netherlands"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Thomas","family":"Bakkum","sequence":"additional","affiliation":[{"name":"Department of Bio-Organic Synthesis Leiden Institute of Chemistry Leiden University  Einsteinweg 55 2333 CC Leiden The Netherlands"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Berend","family":"Gagestein","sequence":"additional","affiliation":[{"name":"Department of Molecular Physiology Leiden Institute of Chemistry Leiden University  Einsteinweg 55 2333 CC Leiden The Netherlands"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Iakovia","family":"Ttofi","sequence":"additional","affiliation":[{"name":"Department of Molecular Physiology Leiden Institute of Chemistry Leiden University  Einsteinweg 55 2333 CC Leiden The Netherlands"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alexi J. 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