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Since the field's beginning, a major focus has been on designing bioorthogonal reagents with good selectivity, reactivity, and stability in complex biological environments. More recently, chemists have imbued reagents with new functionalities like click\u2010and\u2010release or light\/enzyme\u2010controllable reactivity. We have previously developed a controllable cyclopropene\u2010based bioorthogonal ligation, which has excellent stability in physiological conditions and can be triggered to react with tetrazines by exposure to enzymes, biologically significant small molecules, or light spanning the visual spectrum. Here, to improve reactivity and gain a better understanding of this system, we screened diene reaction partners for the cyclopropene. We found that a cyclopropene\u2013quinone pair is 26 times faster than reactions with 1,2,4,5\u2010tetrazines. Additionally, we showed that the reaction of the cyclopropene\u2013quinone pair can be activated by two orthogonal mechanisms: caging group removal on the cyclopropene and oxidation\/reduction of the quinone. Finally, we demonstrated that this caged cyclopropene\u2013quinone can be used as an imaging tool to label the membranes of fixed, cultured cells.<\/jats:p>","DOI":"10.1002\/cbic.202400304","type":"journal-article","created":{"date-parts":[[2024,8,25]],"date-time":"2024-08-25T22:44:06Z","timestamp":1724625846000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Redox\u2010Activated Substrates for Enhancing Activatable Cyclopropene Bioorthogonal Reactions"],"prefix":"10.1002","volume":"25","author":[{"given":"Wei\u2010Siang","family":"Kao","sequence":"first","affiliation":[{"name":"Department of Chemistry Stony Brook University  100 Nicolls Road Stony Brook NY-11794 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wei","family":"Huang","sequence":"additional","affiliation":[{"name":"Department of Chemistry Stony Brook University  100 Nicolls Road Stony Brook NY-11794 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yunlei","family":"Zhang","sequence":"additional","affiliation":[{"name":"Department of Chemistry Stony Brook University  100 Nicolls Road Stony Brook NY-11794 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kangqiao","family":"Wen","sequence":"additional","affiliation":[{"name":"Department of Chemistry Stony Brook University  100 Nicolls Road Stony Brook NY-11794 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Andrea","family":"Meyer","sequence":"additional","affiliation":[{"name":"Department of Chemistry Stony Brook University  100 Nicolls Road Stony Brook NY-11794 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jorge","family":"Escorihuela","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Org\u00e1nica Universitat de Val\u00e8ncia  Avda. 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