Design and synthesis of highly reactive dienophiles for the tetrazine-trans-cyclooctene ligation.
作者： Michael T. Taylor , Melissa L. Blackman , Olga Dmitrenko , Joseph M. Fox
DOI: 10.1021/JA201844C
关键词:
摘要: … -cyclooctene derivative that displays enhanced reactivity in the tetrazine–trans-cycloctene … is 19 and 27 times more reactive than the parent trans-cyclooctene and 4E-cyclooct-4-enol, …
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sci-hub.se 参考文章(48)
Melissa L. Blackman, Maksim Royzen, Joseph M. Fox, Tetrazine ligation: fast bioconjugation based on inverse-electron-demand Diels-Alder reactivity. Journal of the American Chemical Society. ,vol. 130, pp. 13518- 13519 ,(2008) , 10.1021/JA8053805
Robert D. Bach, Ring strain energy in the cyclooctyl system. The effect of strain energy on [3 + 2] cycloaddition reactions with azides. Journal of the American Chemical Society. ,vol. 131, pp. 5233- 5243 ,(2009) , 10.1021/JA8094137
Edmund J. Keliher, Thomas Reiner, Anna Turetsky, Scott A. Hilderbrand, Ralph Weissleder, High-yielding, two-step 18F labeling strategy for 18F-PARP1 inhibitors. ChemMedChem. ,vol. 6, pp. 424- 427 ,(2011) , 10.1002/CMDC.201000426
Venkata R. Krishnamurthy, John T. Wilson, Wanxing Cui, XueZheng Song, Yi Lasanajak, Richard D. Cummings, Elliot L. Chaikof, Chemoselective immobilization of peptides on abiotic and cell surfaces at controlled densities. Langmuir. ,vol. 26, pp. 7675- 7678 ,(2010) , 10.1021/LA101192V
John C. Jewett, Ellen M. Sletten, Carolyn R. Bertozzi, Rapid Cu-free click chemistry with readily synthesized biarylazacyclooctynones. Journal of the American Chemical Society. ,vol. 132, pp. 3688- 3690 ,(2010) , 10.1021/JA100014Q
Ramajeyam Selvaraj, Shuanglong Liu, Matthew Hassink, Chiun-wei Huang, Li-peng Yap, Ryan Park, Joseph M. Fox, Zibo Li, Peter S. Conti, Tetrazine-trans-cyclooctene ligation for the rapid construction of integrin αvβ3 targeted PET tracer based on a cyclic RGD peptide Bioorganic & Medicinal Chemistry Letters. ,vol. 21, pp. 5011- 5014 ,(2011) , 10.1016/J.BMCL.2011.04.116
Maksim Royzen, Glenn P. A. Yap, Joseph M. Fox, A photochemical synthesis of functionalized trans-cyclooctenes driven by metal complexation. Journal of the American Chemical Society. ,vol. 130, pp. 3760- 3761 ,(2008) , 10.1021/JA8001919
Jeet Kalia, Ronald Raines, Advances in Bioconjugation. Current Organic Chemistry. ,vol. 14, pp. 138- 147 ,(2010) , 10.2174/138527210790069839
Franz Thalhammer, Uwe Wallfahrer, Jürgen Sauer, Reaktivität einfacher offenkettiger und cyclischer dienophile bei Diels-Alder-reaktionen mit inversem elektronenbedarf Tetrahedron Letters. ,vol. 31, pp. 6851- 6854 ,(1990) , 10.1016/S0040-4039(00)97188-0
Reyna K. V. Lim, Qing Lin, Bioorthogonal chemistry: recent progress and future directions Chemical Communications. ,vol. 46, pp. 1589- 1600 ,(2010) , 10.1039/B925931G