Rapid Site-Specific Protein Labeling Based on Diels-Alder Bioorthogonal Reactions

doi:10.6023/A12090629

Acta Chimica Sinica ›› 2012, Vol. 70 ›› Issue (21): 2208-2212.DOI: 10.6023/A12090629 Previous Articles Next Articles

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基于Diels-Alder生物正交反应的蛋白质快速位点特异性标记方法

王玥, 叶新山

北京大学医学部天然药物及仿生药物国家重点实验室北京 100191

投稿日期:2012-09-05 发布日期:2012-09-28
通讯作者: 叶新山 E-mail:xinshan@bjmu.edu.cn
基金资助:
项目受科技部“973”计划(No. 2012CB822100)和“重大新药创制”科技重大专项(No. 2012ZX09502001-001)资助.

Rapid Site-Specific Protein Labeling Based on Diels-Alder Bioorthogonal Reactions

Wang Yue, Ye Xinshan

State Key Laboratory of Natural and Biomimetic Drugs, Peking University Health Science Center, Beijing 100191

Received:2012-09-05 Published:2012-09-28
Supported by:
Project supported by the National Basic Research Program of China (973 Program) (No. 2012CB822100) and the National Major Scientific and Technological Special Project for “Significant New Drugs Development” (No. 2012ZX09502001-001).

In recent years, many achievements have been made in site-specific protein modifications. This review highlights the latest advances on protein labeling, which utilizes the inverse electron-demand Diels-Alder bioorthogonal reactions of highly strained alkenes or alkynes and tetrazines, by genetically encoding unnatural amino acids containing one of these functionalities into the specific sites of proteins, leading to the rapid fluorescence labeling of cellular proteins.

Key words: protein labeling, fluorescence probe, bioorthogonal reactions, tetrazine, genetic encoding, unnatural amino acid

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Wang Yue, Ye Xinshan. Rapid Site-Specific Protein Labeling Based on Diels-Alder Bioorthogonal Reactions[J]. Acta Chimica Sinica, 2012, 70(21): 2208-2212.

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[1] Heim, R.; Prasher, D. C.; Tsien, R. Y. Proc. Natl. Acad. Sci. U. S. A. 1994, 91, 12501.
[2] Keppler, A.; Gendreizig, S.; Gronemeyer, T.; Pick, H.; Vogel, H.; Johnsson, K. Nat. Biotech. 2003, 21, 86.
[3] (a) Fernandez-Suarez, M.; Baruah, H.; Martinez-Hernandez, L.; Xie, K. T.; Baskin, J. M.; Bertozzi, C. R.; Ting, A. Y. Nat. Biotech. 2007, 25, 1483; (b) Yao, J. Z.; Uttamapinant, C.; Poloukhtine, A.; Baskin, J. M.; Codelli, J. A.; Sletten, E. M.; Bertozzi, C. R.; Popik, V. V.; Ting, A. Y. J. Am. Chem. Soc. 2012, 134, 3720.
[4] Griffin, B. A.; Adams, S. R.; Tsien, R. Y. Science 1998, 281, 269.
[5] Xie, J.; Schultz, P. G. Methods 2005, 36, 227.
[6] Agard, N. J.; Baskin, J. M.; Prescher, J. A.; Lo, A.; Bertozzi, C. R. ACS Chem. Biol. 2006, 1, 644.
[7] Jewett, J. C.; Sletten, E. M.; Bertozzi, C. R. J. Am. Chem. Soc. 2010, 132, 3688.
[8] (a) Nguyen, D. P.; Elliott, T.; Holt, M.; Muir, T. W.; Chin, J. W. J. Am. Chem. Soc. 2011, 133, 11418; (b) Wang, Y.; Song, W.; Hu, W. J.; Lin, Q. Angew. Chem., Int. Ed. 2009, 48, 5330.
[9] (a) Devaraj, N. K.; Weissleder, R.; Hilderbrand, S. A. Bioconjugate Chem. 2008, 19, 2297; (b) Blackman, M. L.; Royzen, M.; Fox, J. M. J. Am. Chem. Soc. 2008, 130, 13518; (c) Chen, W.; Wang, D.; Dai, C.; Hamelberg, D.; Wang, B. Chem. Commun. 2012, 48, 1736.
[10] Lang, K.; Davis, L.; Torres-Kolbus, J.; Chou, C.; Deiters, A.; Chin, J. W. Nat. Chem. 2012, 4, 298.
[11] Seitchik, J. L.; Peeler, J. C.; Taylor, M. T.; Blackman, M. L.; Rhoads, T. W.; Cooley, R. B.; Refakis, C.; Fox, J. M.; Mehl, R. A. J. Am. Chem. Soc. 2012, 134, 2898.
[12] Plass, T.; Milles, S.; Koehler, C.; Szymański, J.; Mueller, R.; Wieβler, M.; Schultz, C.; Lemke, E. A. Angew. Chem., Int. Ed. 2012, 51, 4166.
[13] Lang, K.; Davis, L.; Wallace, S.; Mahesh, M.; Cox, D. J.; Blackman, M. L.; Fox, J. M.; Chin, J. W. J. Am. Chem. Soc. 2012, 134, 10317.
[14] Rossin, R.; Renart Verkerk, P.; van den Bosch, S. M.; Vulders, R. C. M.; Verel, I.; Lub, J.; Robillard, M. S. Angew. Chem., Int. Ed. 2010, 49, 3375.
[15] Yu, Z.; Pan, Y.; Wang, Z.; Wang, J.; Lin, Q. Angew. Chem., Int. Ed. 2012, doi: 10.1002/anie.201205352.

基于Diels-Alder生物正交反应的蛋白质快速位点特异性标记方法

Rapid Site-Specific Protein Labeling Based on Diels-Alder Bioorthogonal Reactions

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