000058461 001__ 58461 000058461 005__ 20190709135425.0 000058461 0247_ $$2doi$$a10.1002/anie.201609607 000058461 0248_ $$2sideral$$a97502 000058461 037__ $$aART-2017-97502 000058461 041__ $$aeng 000058461 100__ $$aJiménez-Moreno, E. 000058461 245__ $$aVinyl Ether/Tetrazine Pair for the Traceless Release of Alcohols in Cells 000058461 260__ $$c2017 000058461 5060_ $$aAccess copy available to the general public$$fUnrestricted 000058461 5203_ $$aThe cleavage of a protecting group from a protein or drug under bioorthogonal conditions enables accurate spatiotemporal control over protein or drug activity. Disclosed herein is that vinyl ethers serve as protecting groups for alcohol-containing molecules and as reagents for bioorthogonal bond-cleavage reactions. A vinyl ether moiety was installed in a range of molecules, including amino acids, a monosaccharide, a fluorophore, and an analogue of the cytotoxic drug duocarmycin. Tetrazine-mediated decaging proceeded under biocompatible conditions with good yields and reasonable kinetics. Importantly, the nontoxic, vinyl ether duocarmycin double prodrug was successfully decaged in live cells to reinstate cytotoxicity. This bioorthogonal reaction presents broad applicability and may be suitable for in vivo applications. 000058461 536__ $$9info:eu-repo/grantAgreement/ES/MICINN/RYC-2013-14706$$9info:eu-repo/grantAgreement/ES/MINECO/CTQ2015-70524-R 000058461 540__ $$9info:eu-repo/semantics/openAccess$$aby$$uhttp://creativecommons.org/licenses/by/3.0/es/ 000058461 590__ $$a12.102$$b2017 000058461 591__ $$aCHEMISTRY, MULTIDISCIPLINARY$$b14 / 171 = 0.082$$c2017$$dQ1$$eT1 000058461 592__ $$a6.155$$b2017 000058461 593__ $$aChemistry (miscellaneous)$$c2017$$dQ1 000058461 593__ $$aCatalysis$$c2017$$dQ1 000058461 655_4 $$ainfo:eu-repo/semantics/article$$vinfo:eu-repo/semantics/publishedVersion 000058461 700__ $$aGuo, Z. 000058461 700__ $$aOliveira, B.L. 000058461 700__ $$aAlbuquerque, I.S. 000058461 700__ $$aKitowski, A. 000058461 700__ $$aGuerreiro, A. 000058461 700__ $$aBoutureira, O. 000058461 700__ $$aRodrigues, T. 000058461 700__ $$0(orcid)0000-0003-0105-4337$$aJiménez-Osés, G. 000058461 700__ $$aBernardes, G.J.L. 000058461 773__ $$g56, 1 (2017), 243-247$$pAngew. Chem.$$tANGEWANDTE CHEMIE-INTERNATIONAL EDITION$$x1433-7851 000058461 8564_ $$s833687$$uhttps://zaguan.unizar.es/record/58461/files/texto_completo.pdf$$yVersión publicada 000058461 8564_ $$s121364$$uhttps://zaguan.unizar.es/record/58461/files/texto_completo.jpg?subformat=icon$$xicon$$yVersión publicada 000058461 909CO $$ooai:zaguan.unizar.es:58461$$particulos$$pdriver 000058461 951__ $$a2019-07-09-11:28:36 000058461 980__ $$aARTICLE