A biocompatible condensation reaction for the labeling of terminal cysteine residues on proteins

Angewandte Chemie - International Edition

Volumn 48, Issue 51, 2009, Pages 9658-9662

  Ren, Hongjun ^a   Xiao, Fei ^a   Zhan, Ke ^a   Kim, Young Pil ^a   Xie, Hexin ^a   Xia, Zuyong ^a   Rao, Jianghong ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

Chemical ligation; Condensation; Fluorescent probes; Live cell imaging; Protein modifications

Indexed keywords

CHEMICAL LIGATION; DEGREE OF SPECIFICITY; FLUORESCENCE LABELING; FLUORESCENT PROBES; IN-VITRO; LABELING METHODS; LIGATION REACTIONS; LIVE CELL; LIVE-CELL IMAGING; N-TERMINALS; PHYSIOLOGICAL CONDITION; PROTEIN MODIFICATIONS; RHODAMINE DYES; SMALL MOLECULES; TERMINAL CYSTEINE; TOBACCO ETCH VIRUS;

AMINES; AMINO ACIDS; CHEMICAL MODIFICATION; CONDENSATION; CONDENSATION REACTIONS; FLUORESCENCE; LABELING; ORGANIC ACIDS; PROBES;

PROTEINS;

BENZOTHIAZOLE; BENZOTHIAZOLE DERIVATIVE; BOVINE SERUM ALBUMIN; CYSTEINE; FLUORESCENT DYE; LUCIFERASE; LYSOZYME; PROTEIN; PROTEINASE; TEV PROTEASE;

ANIMAL; ARTICLE; CATTLE; CHEMISTRY; HELA CELL; HUMAN; METABOLISM;

ANIMALS; BENZOTHIAZOLES; CATTLE; CYSTEINE; ENDOPEPTIDASES; FLUORESCENT DYES; HELA CELLS; HUMANS; LUCIFERASES; MURAMIDASE; PROTEINS; SERUM ALBUMIN, BOVINE;

EID: 71949087146     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200903627     Document Type: Article

References (48)

1. a) R. Y. Tsien, Annu. Rev. Biochem. 1998, 67, 509;
2. b) K. M. Marks, G. P. Nolan, Nat. Methods 2006, 3, 591;
3. c) N. Johnsson, K. Johnsson, ACS Chem. Biol. 2007, 2, 31;
4. d) A. DragulescuAndrasi, J. Rao, ChemBioChem 2007, 8, 1099;
5. e) M. FernandezSuarez, A. Y. Ting, Nat. Rev. Mol. Cell Biol. 2008, 9, 929.
6. a) A. Keppler, S. Gendreizig, T. Gronemeyer, H. Pick, H. Vogel, K. Johnsson, Nat. Biotechnol. 2003, 21, 86;
7. b) L. W. Miller, J. Sable, P. Goelet, M. P. Sheetz, V. W. Cornish, Angew. Chem. 2004, 116, 1704;
8. Angew. Chem. Int. Ed. 2004, 43, 1672;
9. c) G. V. Los, L. P. Encell, M. G. McDougall, D. D. Hartzeil, N. Karassina, C. Zimprich, M. G. Wood, R. Learish, R. F. Ohane, M. Urh, D. Simpson, J. Mendez, K. Zimmerman, P. Otto, G. Vidugiris, J. Zhu, A. Darzins, D. H. Klaubert, R. F. Bulleit, K. V. Wood, ACS Chem. Biol. 2008, 3, 373;
10. d) S. Mizukami, S. Watanabe, Y. Hori, K. Kikuchi, J. Am. Chem. Soc. 2009, 131, 5016.
11. a) B. A. Griffin, S. R. Adams, R. Y. Tsien, Science 1998, 281, 269;
12. b) T. Wang, P. Yan, T. C. Squier, M. U. Mayer, ChemBiochem 2007, 8, 1937;
13. c) C. T. Hauser, R. Y. Tsien, Proc. Natl. Acad. Sci. USA 2007, 104, 3693
14. d) E. G. Guignet, R. Hovius, H. Vogel, Nat. Biotechnol. 2004, 22, 440;
15. e) Y. Yano, A. Yano, S. Oishi, Y. Sugimoto, G Tsujimoto, N. Fujii, K. Matsuzaki, ACS Chem. Biol. 2008, 3, 341;
16. f) A. Ojida, K. Honda, D. Shinmi, S. Kiyonaka, Y. Mori, I. Hamachi, J. Am. Chem. Soc. 2006, 128, 10452;
17. g) T. L. Halo, J. Appelbaum, E. M. Hobert, D. M. Balkin, A. Schepartz, J. Am. Chem. Soc. 2009, 131, 438.
18. a) I. Chen, M. Howarth, W Lin, A. Y. Ting, Nat Methods 2005, 2, 99;
19. b) L. Vivero-Pol, N. George, H. Krumm, K. Johnsson, N. Johnsson, J. Am. Chem. Soc. 2005, 127, 12770;
20. c) J. Yin, F. Liu, X. Li, C. T. Walsh, J. Am. Chem. Soc. 2004, 126, 7754;
21. d) K. M. Clarke, A. C. Mercer, J. J. La Clair, M. D. Burkart, J. Am. Chem. Soc. 2005, 127, 11234;
22. e) T. Tanaka, T. Yamamoto, S. Tsukiji, T. Nagamune, ChemBioChem 2008, 9, 802;
23. f) Z. Zhou, P. Cironi, A. J. Lin, Y. Xu, S. Hrvatin, D. E. Golan, P. A. Silver, C. T. Walsh, J. Yin, ACS Chem. Biol. 2007, 2, 337;
24. g) C. Gauchet, G. R. Labadie, C. D. Poulter, J. Am. Chem. Soc. 2006, 128, 9274;
25. h) B. P. Duckworth, J. Xu, T. A. Taton, A. Guo, M. D. Distefano, Bioconjugate Chem. 2006, 17, 967.
26. E. Saxon, C. R. Bertozzi, Science 2000, 257, 2007.
27. a) H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. 2001, 113, 2056;
28. Angew. Chem. Int. Ed. 2001, 40, 2004;
29. b) A. J. Link, D A. Tirrell, J. Am. Chem. Soc. 2003, 125, 11164;
30. c) N. J. Agard, J. A. Prescher, C. R. Bertozzi, J. Am. Chem. Soc. 2004, 126, 15046.
31. L. K. Mahal, K. J. Yarema, C. R. Bertozzi, Science 1997, 276, 1125.
32. a) P. E. Dawson, S. B. Kent, Annu. Rev. Biochem. 2000, 69, 923;
33. b) P. E. Dawson, T.W. Muir, I. Clark-Lewis, S. B. H. Kent, Science 1994, 266, 776;
34. c) J. Xiao, A. Burn, T. J. Tolbert, Bioconjugate Chem. 2008, 19, 1113;
35. d) I. E. Gentle, D.P. De Souza, M. Baca, Bioconjugate Chem. 2004, 15, 658;
36. e) J. B. Blanco-Canosa, P. E. Dawson, Angew. Chem. 2008, 120, 6957;
37. Angew. Chem. Int. Ed. 2008, 47, 6851;
38. f) D. A. Erlanson, M. Chytil, G. L. Verdine, Chem. Biol. 1996, 3, 981.
39. a) T. W. Muir, Annu. Rev. Biochem. 2003, 72, 249;
40. b) D. S. Y. Yeo, R. Srinivasan, G. Y. J. Chen, S. Q. Yao, Chem. Eur. J 2004, 10, 4664;
41. c) V. Muralidharan, T. W Muir, Nat Methods 2006, 3, 429.
42. a) D. S. Y. Yeo, R. Srinivasan, M. Uttamchandani, G. Y. J. Chen, Q. Zhu, S. Q. Yao, Chem. Commun. 2003, 2870;
43. b) G. K. Busch, E. W. Tate, P. R. J. Gaffney, E. Rosivatz, R. Woscholski, R. J. Leatherbarrow, Chem. Commun. 2008, 3369;
44. c) S. Chattopadhaya, R. Srinivasan, D S. Y. Yeo, G.Y.J. Chen, S. Q. Yao, Bioorg. Med. Chem. 2009, 17, 981.
45. E. H. White, F. McCapra, G. F. Field, W. D. McElroy, J. Am. Chem. Soc. 1961, 83, 2402.
46. J. M. Baskin, J. A. Prescher, S. T. Laughlin, N. J. Agard, P. V. Chang, I. A. Miller, A. Lo, J. A. Codelli, C. R. Bertozzi, Proc. Natl. Acad. Sci. USA 2007, 104, 16793.
47. a) A. Telenti, M. Southworth, F. Alcaide, S. Daugelat, W. R. Jacobs, Jr., F. B. Perler, J. Bacteriol. 1997, 179, 6378;
48. b) Z. Xia, Y. Xing, M.-K. So, A. L. Koh, R. Sinclair, J. Rao, Anal. Chem. 2008, 80, 8649.