Fast, cell-compatible click chemistry with copper-chelating azides for biomolecular labeling

Angewandte Chemie - International Edition

Volumn 51, Issue 24, 2012, Pages 5852-5856

  Uttamapinant, Chayasith ^a   Tangpeerachaikul, Anupong ^a   Grecian, Scott ^b   Clarke, Scott ^b   Singh, Upinder ^b   Slade, Peter ^b   Gee, Kyle R ^b   Ting, Alice Y ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^b Life Technologies   (United States)

Author keywords

click chemistry; fluorescent probes; lipoic acid ligase; metabolic labeling; protein engineering

Indexed keywords

CLICK CHEMISTRY; FLUORESCENT PROBES; LIPOIC ACIDS; METABOLIC LABELING; PROTEIN ENGINEERING;

ACETYLENE; CHELATION; GENETIC ENGINEERING; NITROGEN COMPOUNDS; RNA; SYNTHESIS (CHEMICAL);

COPPER;

ALKYNE; AZIDE; CHELATING AGENT; COPPER; FLUORESCENT DYE; PROTEIN; RNA;

ARTICLE; CATALYSIS; CHEMISTRY; CLICK CHEMISTRY; PROTEIN ENGINEERING;

ALKYNES; AZIDES; CATALYSIS; CHELATING AGENTS; CLICK CHEMISTRY; COPPER; FLUORESCENT DYES; PROTEIN ENGINEERING; PROTEINS; RNA;

EID: 84861912742     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201108181     Document Type: Article

References (27)

1. J. E. Moses, A. D. Moorhouse, Chem. Soc. Rev. 2007, 36, 1249-1262.
2. V. Hong, N. F. Steinmetz, M. Manchester, M. G. Finn, Bioconjugate Chem. 2010, 21, 1912-1916.
3. J. C. Jewett, C. R. Bertozzi, Chem. Soc. Rev. 2010, 39, 1272-1279.
4. N. E. Mbua, J. Guo, M. A. Wolfert, R. Steet, G. J. Boons, ChemBioChem 2011, 12, 1912-1920.
5. A. Kuzmin, A. Poloukhtine, M. A. Wolfert, V. V. Popik, Bioconjugate Chem. 2010, 21, 2076-2085.
6. J. C. Jewett, E. M. Sletten, C. R. Bertozzi, J. Am. Chem. Soc. 2010, 132, 3688-3690.
7. S. I. Presolski, V. Hong, S. H. Cho, M. G. Finn, J. Am. Chem. Soc. 2010, 132, 14570-14576.
8. V. Hong, S. I. Presolski, C. Ma, M. G. Finn, Angew. Chem. 2009, 121, 10063-10067
9. Angew. Chem. Int. Ed. 2009, 48, 9879-9883.
10. C. Besanceney-Webler, H. Jiang, T. Q. Zheng, L. Feng, D. S. delAmo, W. Wang, L. M. Klivansky, F. L. Marlow, Y. Liu, Wu, Angew. Chem. 2011, 123, 8201-8206
11. Angew. Chem. Int. Ed. 2011, 50, 8051-8056.
12. D. C. Kennedy, C. S. McKay, M. C. B. Legault, D. C. Danielson, J. A. Blake, A. F. Pegoraro, A. Stolow, Z. Mester, J. P. Pezacki, J. Am. Chem. Soc. 2011, 133, 17993-18001.
13. W. S. Brotherton, H. A. Michaels, J. T. Simmons, R. J. Clark, N. S. Dalal, L. Zhu, Org. Lett. 2009, 11, 4954-4957.
14. G. C. Kuang, H. A. Michaels, J. T. Simmons, R. J. Clark, L. Zhu, J. Org. Chem. 2010, 75, 6540-6548.
15. C. Y. Jao, A. Salic, Proc. Natl. Acad. Sci. USA 2008, 105, 15779-15784.
16. K. E. Beatty, F. Xie, Q. Wang, D. A. Tirrell, J. Am. Chem. Soc. 2005, 127, 14150-14151.
17. F. Himo, T. Lovell, R. Hilgraf, V. V. Rostovtsev, L. Noodleman, K. B. Sharpless, V. V. Fokin, J. Am. Chem. Soc. 2005, 127, 210-216.
18. Z. Zhou, C. J. Fahrni, J. Am. Chem. Soc. 2004, 126, 8862-8863.
19. C. Uttamapinant, K. A. White, H. Baruah, S. Thompson, M. Fernandez-Suarez, S. Puthenveetil, A. Y. Ting, Proc. Natl. Acad. Sci. USA 2010, 107, 10914-10919.
20. H. Baruah, S. Puthenveetil, Y. A. Choi, S. Shah, A. Y. Ting, Angew. Chem. 2008, 120, 7126-7129
21. Angew. Chem. Int. Ed. 2008, 47, 7018-7021.
22. X. Jin, C. Uttamapinant, A. Y. Ting, ChemBioChem 2011, 12, 65-70.
23. S. Puthenveetil, D. S. Liu, K. A. White, S. Thompson, A. Y. Ting, J. Am. Chem. Soc. 2009, 131, 16430-16438.
24. D. S. delAmo, W. Wang, H. Jiang, C. Besanceney, A. C. Yan, M. Levy, Y. Liu, F. L. Marlow, Wu, J. Am. Chem. Soc. 2010, 132, 16893-16899.
25. J. Z. Yao, C. Uttamapinant, A. Poloukhtine, J. M. Baskin, J. A. Codelli, E. M. Sletten, C. R. Bertozzi, V. V. Popik, A. Y. Ting, J. Am. Chem. Soc. 2012, 134, 3720-3728.
26. X. H. Ning, J. Guo, M. A. Wolfert, G. J. Boons, Angew. Chem. 2008, 120, 2285-2287
27. Angew. Chem. Int. Ed. 2008, 47, 2253-2255.