Simultaneous dual protein labeling using a triorthogonal reagent

Journal of the American Chemical Society

Volumn 135, Issue 44, 2013, Pages 16388-16396

  Rashidian, Mohammad ^a   Kumarapperuma, Sidath C ^a,b   Gabrielse, Kari ^b   Fegan, Adrian ^b   Wagner, Carston R ^b   Distefano, Mark D ^a  

^a University of Minnesota   (United States)

^b UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CILIARY NEUROTROPHIC FACTORS; DIHYDROFOLATE REDUCTASE; ENZYMATICALLY MODIFIED; GREEN FLUORESCENT PROTEIN; HETERO-FUNCTIONAL PROTEINS; MULTIFUNCTIONAL PROTEIN; PHARMACOKINETIC PROFILES; POLYETHYLENE GLYCOL (PEG);

AMINO ACIDS; BIOSYNTHESIS; FLUOROPHORES; NEUROLOGY;

PROTEINS;

ALDEHYDE DERIVATIVE; ALKYNE DERIVATIVE; CILIARY NEUROTROPHIC FACTOR; DIHYDROFOLATE REDUCTASE; GREEN FLUORESCENT PROTEIN; HYBRID PROTEIN; MULTIPROTEIN COMPLEX; NANOMATERIAL; OXIME; REAGENT; TRIORTHOGONAL REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL LABELING; ENZYME MODIFICATION; MACROMOLECULE; PROTEIN ANALYSIS; PROTEIN ASSEMBLY; PROTEIN FUNCTION; PROTEIN MODIFICATION; PROTEIN STRUCTURE;

CILIARY NEUROTROPHIC FACTOR; GREEN FLUORESCENT PROTEINS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; POLYISOPRENYL PHOSPHATES; SESQUITERPENES; STAINING AND LABELING;

EID: 84887747556     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja403813b     Document Type: Article

References (50)

1. Bertozzi, C. R. Acc. Chem. Res. 2011, 44, 651-653
2. Prescher, J. A.; Bertozzi, C. R. Nat. Chem. Biol. 2005, 1, 13-21
3. Mamidyala, S. K.; Finn, M. G. Chem. Soc. Rev. 2010, 39, 1252
4. Christman, K. L.; Broyer, R. M.; Tolstyka, Z. P.; Maynard, H. D. J. Mater. Chem. 2007, 17, 2021
5. Prost, L. R.; Grim, J. C.; Tonelli, M.; Kiessling, L. L. ACS Chem. Biol. 2012, 7, 1603-1608
6. Wang, T.; Kartika, R.; Spiegel, D. A. J. Am. Chem. Soc. 2012, 134, 8958-8967
7. Park, S.; Yousaf, M. N. Langmuir 2008, 24, 6201-6207
8. Keppler, A.; Pick, H.; Arrivoli, C.; Vogel, H.; Johnsson, K. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 9955-9959
9. Yin, J.; Liu, F.; Li, X.; Walsh, C. T. J. Am. Chem. Soc. 2004, 126, 7754-7755
10. Chen, I.; Ting, A. Y. Curr. Opin. Biotechnol. 2005, 16, 35-40
11. Discher, D. E.; Eisenberg, A. Science 2002, 297, 967-973
12. Kim, C. H.; Axup, J. Y.; Dubrovska, A.; Kazane, S. A.; Hutchins, B. A.; Wold, E. D.; Smider, V. V.; Schultz, P. G. J. Am. Chem. Soc. 2012, 9918-9921
13. Hudak, J. E.; Barfield, R. M.; de Hart, G. W.; Grob, P.; Nogales, E.; Bertozzi, C. R.; Rabuka, D. Angew. Chem., Int. Ed. 2012, 51, 4161-4165
14. Witte, M. D.; Cragnolini, J. J.; Dougan, S. K.; Yoder, N. C.; Popp, M. W.; Ploegh, H. L. Proc. Natl. Acad. Sci. U. S. A. 2012, 109, 11993-11998
15. Yi, L.; Sun, H.; Itzen, A.; Triola, G.; Waldmann, H.; Goody, R. S.; Wu, Y.-W. Angew. Chem., Int. Ed. Engl. 2011, 50, 8287-8290
16. Brustad, E. M.; Lemke, E. A.; Schultz, P. G.; Deniz, A. A. J. Am. Chem. Soc. 2008, 130, 17664-17665
17. Kim, J.; Seo, M.-H.; Lee, S.; Cho, K.; Yang, A.; Woo, K.; Kim, H.-S.; Park, H.-S. Anal. Chem. 2013, 85, 1468-1474
18. Feng, L.; Hong, S.; Rong, J.; You, Q.; Dai, P.; Huang, R.; Tan, Y.; Hong, W.; Xie, C.; Zhao, J.; Chen, X. J. Am. Chem. Soc. 2013, 135, 9244-9247
19. Rashidian, M.; Dozier, J. K.; Lenevich, S.; Distefano, M. D. Chem. Commun. 2010, 46, 8998
20. Weinrich, D.; Lin, P.-C.; Jonkheijm, P.; Nguyen, U. T. T.; Schröder, H.; Niemeyer, C. M.; Alexandrov, K.; Goody, R.; Waldmann, H. Angew. Chem., Int. Ed. 2010, 49, 1252-1257
21. Gauchet, C.; Labadie, G. R.; Poulter, C. D. J. Am. Chem. Soc. 2006, 128, 9274-9275
22. Kim, M.; Kleckley, T. S.; Wiemer, A. J.; Holstein, S. A.; Hohl, R. J.; Wiemer, D. F. J. Org. Chem. 2004, 69, 8186-8193
23. Rashidian, M.; Song, J. M.; Pricer, R. E.; Distefano, M. D. J. Am. Chem. Soc. 2012, 134, 8455-8467
24. Placzek, A. T.; Gibbs, R. A. Org. Lett. 2011, 3576-3579
25. Labadie, G. R.; Viswanathan, R.; Poulter, C. D. J. Org. Chem. 2007, 72, 9291-9297
26. Subramanian, T.; Liu, S.; Troutman, J. M.; Andres, D. A.; Spielmann, H. P. ChemBioChem 2008, 9, 2872-2882
27. Duckworth, B. P.; Xu, J.; Taton, T. A.; Guo, A.; Distefano, M. D. Bioconjugate Chem. 2006, 17, 967-974
28. Li, Q.; So, C. R.; Fegan, A.; Cody, V.; Sarikaya, M.; Vallera, D. A.; Wagner, C. R. J. Am. Chem. Soc. 2010, 48, 17247-17257
29. Sonogashira, K. J. Organomet. Chem. 2002, 653, 46-49
30. Pompliano, D. L.; Gomez, R. P.; Anthony, N. J. J. Am. Chem. Soc. 1992, 114, 7945-7946
31. Rashidian, M.; Mahmoodi, M. M.; Shah, R.; Dozier, J. K.; Wagner, C. R.; Distefano, M. D. Bioconjugate Chem. 2013, 24, 333-342
32. Ip, N. Y.; Yancopoulos, G. D. Annu. Rev. Neurosci. 1996, 19, 491-515
33. Rhee, K. D.; Yang, X.-J. Adv. Exp. Med. Biol. 2010, 664, 647-654
34. Wen, R.; Tao, W.; Li, Y.; Sieving, P. A. Prog. Retinal Eye Res. 2012, 31, 136-151
35. Rothemund, P. W. K. Nature 2006, 440, 297-302
36. Pistol, C.; Dwyer, C. Nanotechnology 2007, 18, 125305
37. Guo, P. Nat. Nanotechnol. 2010, 5, 833-842
38. Ke, Y.; Lindsay, S.; Chang, Y.; Liu, Y.; Yan, H. Science 2008, 319, 180-183
39. Matsuura, K.; Watanabe, K.; Matsuzaki, T.; Sakurai, K.; Kimizuka, N. Angew. Chem., Int. Ed. 2010, 49, 9662-9665
40. Salgado, E. N.; Radford, R. J.; Tezcan, F. A. Acc. Chem. Res. 2010, 43, 661-672
41. Hu, M.; Qian, L.; Briñas, R. P.; Lymar, E. S.; Hainfeld, J. F. Angew. Chem., Int. Ed. Engl. 2007, 46, 5111-5114
42. Chen, G.; Jiang, M. Chem. Soc. Rev. 2011, 40, 2254
43. Uhlenheuer, D. A.; Petkau, K.; Brunsveld, L. Chem. Soc. Rev. 2010, 39, 2817
44. Lai, J. R.; Fischbach, M. A.; Liu, D. R.; Walsh, C. T. J. Am. Chem. Soc. 2006, 128, 11002-11003
45. Fegan, A.; White, B.; Carlson, J. C. T.; Wagner, C. R. Chem. Rev. 2010, 110, 3315-3336
46. Carlson, J. C. T.; Jena, S. S.; Flenniken, M.; Chou, T.; Siegel, R. A.; Wagner, C. R. J. Am. Chem. Soc. 2006, 128, 7630-7638
47. Li, Q.; Hapka, D.; Chen, H.; Vallera, D. A.; Wagner, C. R. Angew. Chem., Int. Ed. 2008, 47, 10179-10182
48. Fegan, A.; Kumarapperuma, S. C.; Wagner, C. R. Mol. Pharmaceutics 2012, 9, 3218-3227
49. Gangar, A.; Fegan, A.; Kumarapperuma, S. C.; Wagner, C. R. J. Am. Chem. Soc. 2012, 134, 2895-2897
50. Viault, G.; Dautrey, S.; Maindron, N.; Hardouin, J.; Renard, P.-Y.; Romieu, A. Org. Biomol. Chem. 2013, 11, 2693-2705