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• W2799384328 abstract "The bioorthogonal cleavage of allylic carbamates from trans-cyclooctene (TCO) upon reaction with tetrazine is widely used to release amines. We disclose herein that this reaction can also cleave TCO esters, carbonates, and surprisingly, ethers. Mechanistic studies demonstrated that the elimination is mainly governed by the formation of the rapidly eliminating 1,4-dihydropyridazine tautomer, and less by the nature of the leaving group. In contrast to the widely used p-aminobenzyloxy linker, which affords cleavage of aromatic but not of aliphatic ethers, the aromatic, benzylic, and aliphatic TCO ethers were cleaved as efficiently as the carbamate, carbonate, and esters. Bioorthogonal ether release was demonstrated by the rapid uncaging of TCO-masked tyrosine in serum, followed by oxidation by tyrosinase. Finally, tyrosine uncaging was used to chemically control cell growth in tyrosine-free medium." @default.
• W2799384328 created "2018-05-17" @default.
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• W2799384328 date "2018-08-13" @default.
• W2799384328 modified "2023-10-03" @default.
• W2799384328 title "Click‐to‐Release from <i>trans</i> ‐Cyclooctenes: Mechanistic Insights and Expansion of Scope from Established Carbamate to Remarkable Ether Cleavage" @default.
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• W2799384328 doi "https://doi.org/10.1002/anie.201800402" @default.
• W2799384328 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/29746709" @default.
• W2799384328 hasPublicationYear "2018" @default.
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