Page 64 - Tyrosine-Based Bioconjugations - Jorick Bruins
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Chapter 3
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(19) Sen, R., Escorihuela, J., van Delft, F., and Zuilhof, H., Rapid and Complete Surface
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(20) Albada, H. B., Wieberneit, F., Dijkgraaf, I., Harvey, J. H., Whistler, J. L., Stoll, R., Metzler-
Nolte, N., and Fish, R. H., The Chemoselective Reactions of Tyrosine-Containing G-Protein- Coupled Receptor Peptides with [Cp*Rh(H2O)(3)](OTf)(2), Including 2D NMR Structures and the Biological Consequences. J. Am. Chem. Soc. 2012, 134 (25), 10321-4.
(21) Ohata, J., Miller, M. K., Mountain, C. M., Vohidov, F., and Ball, Z. T., A Three-Component Organometallic Tyrosine Bioconjugation. Angewandte Chemie-International Edition 2018, 57 (11), 2827-30.
(22) Taylor, M. T., Blackman, M. L., Dmitrenko, O., and Fox, J. M., Design and Synthesis of Highly Reactive Dienophiles for the Tetrazine trans-Cyclooctene Ligation. J. Am. Chem. Soc. 2011, 133 (25), 9646-9.
(23) Bruins, J. J., Albada, B., and van Delft, F., ortho-Quinones and Analogues Thereof: Highly Reactive Intermediates for Fast and Selective Biofunctionalization. Chem. - Eur. J. 2018, 24 (19), 4749-56.
(24) Garcia-Molina, F., Hiner, A. N. P., Fenoll, L. G., Rodriguez-Lopez, J. N., Garcia-Ruiz, P. A., Garcia-Canovas, F., and Tudela, J., Mushroom tyrosinase: Catalase activity, inhibition, and suicide inactivation. J. Agric. Food. Chem. 2005, 53 (9), 3702-9.
(25) Dommerholt, J., Schmidt, S., Temming, R., Hendriks, L. J. A., Rutjes, F. P. J. T., van Hest, J. C. M., Lefeber, D. J., Friedl, P., and van Delft, F. L., Readily accessible bicyclononynes for bioorthogonal labeling and three-dimensional imaging of living cells. Angew. Chem. Int. Ed. 2010, 49 (49), 9422-5.
(26) Gahtory, D., Sen, R., Kuzmyn, A. R., Escorihuela, J., and Zuilhof, H., Strain-Promoted Cycloaddition of Cyclopropenes with o-Quinones: A Rapid Click Reaction. Angew. Chem., Int. Ed. 2018, 57 (32), 10118-22.
(27) Lang, K., Davis, L., Wallace, S., Mahesh, M., Cox, D. J., Blackman, M. L., Fox, J. M., and Chin, J. W., Genetic Encoding of Bicyclononynes and trans-Cyclooctenes for Site-Specific Protein Labeling in Vitro and in Live Mammalian Cells via Rapid Fluorogenic Diels-Alder Reactions. J. Am. Chem. Soc. 2012, 134 (25), 10317-20.
(28) Rossin, R., van den Bosch, S. M., Ten Hoeve, W., Carvelli, M., Versteegen, R. M., Lub, J., and Robillard, M. S., Highly reactive trans-cyclooctene tags with improved stability for Diels- Alder chemistry in living systems. Bioconjug Chem 2013, 24 (7), 1210-7.
(29) Darko, A., Wallace, S., Dmitrenko, O., Machovina, M. M., Mehl, R. A., Chin, J. W., and Fox, J. M., Conformationally strained trans-cyclooctene with improved stability and excellent reactivity in tetrazine ligation. Chem. Sci. 2014, 5 (10), 3770-6.
(30) van Geel, R., Wijdeven, M. A., Heesbeen, R., Verkade, J. M. M., Wasiel, A. A., van Berkel, S. S., and van Delft, F. L., Chemoenzymatic Conjugation of Toxic Payloads to the Globally Conserved N-Glycan of Native mAbs Provides Homogeneous and Highly Efficacious Antibody-Drug Conjugates. Bioconjugate Chem. 2015, 26 (11), 2233-42.
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