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Although linkages thus formed are mostly passive, some of them have shown to significantly contribute to the protein binding through for instance hydrogen bonding and stacking interactions. Biocompatible reactions and click chemistry are a formidable source of inspiration for developing such new protein\u2010directed ligations. This study reports a proximity\u2010induced thiol\u2010yne synthesis of carbonic anhydrase inhibitors. Not only this example widens the arsenal of kinetic target\u2010guided synthesis (KTGS) eligible reactions, but the obtained product displayed unsuspected photophysical properties. The corresponding vinyl sulfide linkage conjugated to a coumarin core proved to be engaged in a monodirectional Z to E photoisomerization process. Further investigations guided by theoretical calculations showed that fine\u2010tuning of the nature of the substituents on the coumarin moiety allows to obtain a bidirectional photochemical process, thus discovering a new photoswitching moiety, displaying moreover fluorescence properties. Due to the spectral tunability of coumarin derivatives, this work should open new opportunities for the design of vinyl sulfide\u2010based photoswitch systems with modular photophysical properties.<\/jats:p>","DOI":"10.1002\/chem.202202180","type":"journal-article","created":{"date-parts":[[2022,7,21]],"date-time":"2022-07-21T07:58:32Z","timestamp":1658390312000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Metalloenzyme\u2010Mediated Thiol\u2010Yne Addition Towards Photoisomerizable Fluorescent Dyes"],"prefix":"10.1002","volume":"28","author":[{"given":"Alexis","family":"Lossouarn","sequence":"first","affiliation":[{"name":"Normandie Univ, CNRS, UNIROUEN, INSA Rouen, COBRA (UMR 6014)  Rouen 76000 France"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Chlo\u00e9","family":"Puteaux","sequence":"additional","affiliation":[{"name":"Normandie Univ, CNRS, UNIROUEN, INSA Rouen, COBRA (UMR 6014)  Rouen 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