Expanded utility of the native chemical ligation reaction

Chemistry - A European Journal

Volumn 10, Issue 19, 2004, Pages 4664-4672

  Yeo, Dawn S Y ^a   Srinivasan, Rajavel ^a   Chen, Grace Y J ^a   Yao, Shao Q ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

Bioimaging; Biotinylation; Fluorescence; Intein; Native chemical ligation; Protein modifications

Indexed keywords

CELLS; DNA; GENES; MOLECULAR DYNAMICS; PROTEINS;

IN VIVO PROTEIN BIOTINYLATION; PROTEIN INTERACTION; PROTEIN MICROARRAYS; PROTEOMICS;

BIOTECHNOLOGY;

BIOTIN;

BIOTINYLATION; CHEMICAL REACTION; MOLECULAR PROBE; PROTEIN ANALYSIS; PROTEIN INTERACTION; PROTEIN LOCALIZATION; PROTEIN MICROARRAY; PROTEIN PROCESSING; PROTEIN STABILITY; PROTEIN STRUCTURE; PROTEOMICS; RECOMBINANT DNA TECHNOLOGY; REVIEW; TECHNOLOGY;

BIOCHEMISTRY; BIOTIN; INTEINS; LIGANDS; PROTEIN ARRAY ANALYSIS; PROTEINS; PROTEOMICS;

EID: 5444248441     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400414     Document Type: Review

References (82)

1. a) G. A. Lemieux, C. R. Bertozzi, Trends Biotechnol 1998, 16, 506-513,
2. b) H C Kolb, M. G Finn, K. B. Sharpless, Angew Chem 2001, 113, 2056-2075; Angew Chem Int Ed 2001, 40, 2004-2041,
3. b) H C Kolb, M. G Finn, K. B. Sharpless, Angew Chem 2001, 113, 2056-2075; Angew Chem Int Ed 2001, 40, 2004-2041,
4. c) P. E. Dawson, S. B. H Kent, Annu Rev. Biochem 2000, 69, 923-960
5. d) T. W. Muir, Annu. Rev Biochem 2003, 72, 249-289
6. a) T. Wieland, E. Bokelmann, L. Bauer, H. U. Lang, H. Lau, Justus Liebigs Ann Chem. 1953, 583, 129-139,
7. b) M. Brenner, J. P. Zimmermann, J. Wehrmuller, P. Quitt, A. Hartmann, W. Schneider, U Berlinger, Helv. Chim Acta 1957, 40, 1497-1505,
8. c) P. E Dawson, T W Muir, I dark-Lewis, S. B. H Kent, Science 1994, 266, 776-779.
9. a) J. Offer, C N. C. Boddy, P. E. Dawson, J. Am Chem. Soc 2002, 124, 4642-4646;
10. b) L. Z. Yan, P E Dawson, J Am Chem Soc 2001, 123, 526-533
11. c) T M. Hackeng, J. H. Griffin, P. E Dawson, Proc Natl Acad Sci USA 1999, 96, 10068-10073,
12. d) G S. Beligere, P.E. Dawson, J Am Chem Soc 1999, 121, 6332-6333,
13. e) L. E. Canne, S J Bark, S. B. H. Kent, J. Am Chem Soc 1996, 118, 5891-5896;
14. f) J Offer, P. E. Dawson, Org. Lett 2000, 2, 23-26.
15. Y. G Gololobov, L. F. Kasukhin, Tetrahedron 1992, 48, 1353-1405
16. a) E. Saxon, C.R. Bertozzi, Science 2000, 287, 2007-2010,
17. b) E. Saxon, J. I Armstrong, C. R. Bertozzi, Org Lett. 2000, 2, 2141-2143;
18. c) B. L. Nilsson, L L. Kiessling, R. T. Rames, Org. Lett 2000, 2, 1939-1941;
19. d) B. L Nilsson, R. J. Hondal, M B Soellner, R. T Rames, J Am Chem. Soc 2003, 725, 5268-5269
20. a) Z Zhang, B. A. C Smith, L. Wang, A Brock, C Cho, P. G Schultz, Biochemistry 2003, 42, 6735-6746;
21. b) L. Wang, A Brock, B. Herberich, P G Schultz, Science 2001, 292, 498-500
22. L. K Mahal, K. J. Yarema, C R Bertozzi, Science 1997, 276, 1125-1128
23. V V. Rostovtsev, L G. Green, V V. Fokin, K B. Sharpless, Angew Chem 2002, 114, 2708-2711; Angew Chem Int Ed 2002, 41, 2596-2599.
24. V V. Rostovtsev, L G. Green, V V. Fokin, K B. Sharpless, Angew Chem 2002, 114, 2708-2711; Angew Chem Int Ed 2002, 41, 2596-2599.
25. A. E Speers, G C. Adam, B. F Cravatt, J. Am Chem Soc 2003, 725, 4686-4687
26. H Paulus, Annu Rev Biochem 2000, 69, 447-496.
27. a) K. Severinov, T. W Muir, J Biol Chem. 1998, 275, 16205-16209,
28. b) F I Valiyaveetil, R. MacKinnon, T W. Muir, J Am. Chem. Soc 2002, 124, 9113-9120;
29. c) F. I. Valiyaveetil, M Sekedat, T. W Muir, R MacKinnon, Angew. Chem 2004, 776, 2558-2561; Angew Chem Int Ed 2004, 43, 2504-2507,
30. c) F. I. Valiyaveetil, M Sekedat, T. W Muir, R MacKinnon, Angew. Chem 2004, 776, 2558-2561; Angew Chem Int Ed 2004, 43, 2504-2507,
31. d) Z Machova, R. von Eggelkraut-Gottanka, N Wehofsky, F. Bordusa, A G Beck-Sickmger, Angew. Chem 2003, 775, 5065-5067, Angew Chem Int. Ed 2003, 42, 4916-4918
32. d) Z Machova, R. von Eggelkraut-Gottanka, N Wehofsky, F. Bordusa, A G Beck-Sickmger, Angew. Chem 2003, 775, 5065-5067, Angew Chem Int. Ed 2003, 42, 4916-4918
33. B M Lew, K. V Mills, H Paulus, J. Biol Chem 1998, 275, 15887-15890
34. T Yamazaki, T Otomo, N Oda, Y Kyogoku, K. Uegaki, N Ito, Y Ishmo, H Nakamura, J Am Chem Soc 1998, 720, 5591-5592
35. a) C P Scott, E Abel-Santos, M. Wall, D C Wahnon, S. J. Benkovic, Proc Natl Acad Sci USA 1999, 96, 13638-13643,
36. b) T. C. Evans, D. Martin, R. Kolly, D Panne, L. Sun, I. Ghosh, L Chen, J Benner, X. Q. Liu, M. Q Xu, J. Biol Chem 2000, 275, 9091-9094,
37. c) H. Iwai, A. Lingel, A. Pluckthun, J Biol Chem 2001, 276, 16548-16554
38. a) T. Ozawa, S. Nogami, M. Sato, Y. Ohya, Y. Umezawa, Anal. Chem 2000, 72, 5151-5157,
39. b) T. Ozawa, Y Umezawa, Curr Opin. Chem Biol. 2001, 5, 578-583.
40. I Giriat, T. W Muir, J. Am. Chem Soc 2003, 725, 7180-7181
41. a) M. L. Lesaicherre, R. Y. P Lue, G Y J Chen, Q. Zhu, S Q Yao, J Am Chem Soc. 2002, 124, 8768-8769,
42. b) R Y P Lue, G. Y J Chen, Y Hu, Q Zhu, S. Q. Yao, J Am Chem Soc. 2004, 726, 1055-1062.
43. a) R Y P Lue, D. S Y Yeo, L P Tan, M Uttamchandani, G. Y J. Chen, S Q Yao, in Protein Microarrays (Ed.. M. Schena), Jones and Bartlett, Sudbury, MA, 2004, Chapter 2;
44. b) R. Y. P. Lue, D. S. Y. Yeo, L. P Tan, G. Y. J. Chen, S Q Yao, in Proteomics Handbook (Ed: J Walker), Humana, Totowa, 2004
45. c) DSY Yeo, R Srinivasan, M Uttamchandani, G. Y. J Chen, Q Zhu, S Q Yao,Chem Commun 2003, 2870-2871.
46. M Wilchek, E. A Bayer, Methods Enzymol 1990, 184, 5-13.
47. G T Hermanson, Bioconjugate Techniques, Academic Press, San Diego, CA, 1996
48. J. E Cronan, K E Reed, Methods Enzymol 2000, 527, 440-458
49. M. G. Cull, P J Schatz, Methods Enzymol 2000, 326, 430-440.
50. M Y. He, M J. Taussig, Nucleic Acids Res 2001, 29, e73.
51. a) G MacBeath, S. L Schreiber, Science 2000, 289, 1760-1763,
52. b) G Y. J. Chen, M. Uttamchandani, R. Y P Lue, M L. Lesaicherre, S Q Yao, Curr Top Med Chem 2003, 3, 705-724.
53. a) M. L Lesaicherre, M. Uttamchandani, G Y. J. Chen, S. Q. Yao, Bioorg Med Chem Lett 2002, 12, 2079-2083,
54. b) M. Uttamchandani, E. W. S Chan, G Y J Chen, S. Q. Yao, Bioorg Med Chem Lett. 2003, 13, 2997-3000;
55. c) M Uttanchandani, G Y J. Chen, M L Lesaicherre, S Q Yao, Methods Mol Biol. 2004, 278, 191-204
56. R T. Baker, Curr Opin Biotechnol 1996, 7, 541-546
57. T Tolbert, C. H. Wong, J. Am Chem. Soc 2000, 122, 5421-5428.
58. a) A. Miyawaki, A. Sawano, T Kogure, Nat Cell Biol. 2003, Suppl, S1-S7;
59. b) J. Zhang, R. E Campbell, A. Y Ting, R. Y. Tsien, Nat Rev Mol Cell Biol 2002, 3, 906-918;
60. c) R. Y. Tsien, Annu Rev Biochem 1998, 67, 509-544.
61. a) B. A. Griffin, S. R Adams, R. Y Tsien, Science 1998, 281, 269-272;
62. b) G. Gaietta, T. J Deerinck, S. R. Adams, J Bouwer, O Tour, D W. Laird, G E Sosinsky, R Y Tsien, M H. Ellisman, Science 2002, 296, 503-507.
63. M. M. Wu, J Llopis, S. Adams, J M. McCaffery, M S. Kulomaa, T. E. Machen, H P. Moore, R. Y. Tsien, Chem. Biol. 2000, 7, 197-209.
64. J. Farinas, A. S Verkman, J. Biol. Chem 1999, 274, 7603-7606.
65. A Keppler, S Gendreizig, T. Gronemeyer, H, Pick, H Vogel, K. Johnsson, Nat Biotechnol 2003, 27, 86-89.
66. L W Miller, J. Sable, P Goelet, M. P. Sheetz, V W. Cornish, Angew. Chem 2004, 116, 1704-1707, Angew Chem Int Ed 2004, 43, 1672-1675
67. L W Miller, J. Sable, P Goelet, M. P. Sheetz, V W. Cornish, Angew. Chem 2004, 116, 1704-1707, Angew Chem Int Ed 2004, 43, 1672-1675
68. M. Q Xu, T C Evans, Methods 2001, 24, 257-277.
69. P. H Hirel, J. M. Schmitter, P Dessen, G Fayat, S. Blanquet, Proc Natl Acad Sci USA 1989, 86, 8247-8351.
70. T J Tolbert, C H Wong, Angew Chem 2002, 114, 2275-2278, Angew Chem Int. Ed 2002, 41, 2171-2174
71. T J Tolbert, C H Wong, Angew Chem 2002, 114, 2275-2278, Angew Chem Int. Ed 2002, 41, 2171-2174
72. S Y D Yeo, R Srinivasan, G Y. J Chen, Q. Zhu, S Q. Yao, unpublished results
73. a) J. J. Lee, S C Ekker, D P Kessler, J. A. Porter, B I Sun, P. A. Beachy, Science 1994, 266, 1528-1537;
74. b) J. A Porter, S. C. Ekker, W. J Park, D. P Kessler, K. E Young, C. H Chen, Y Ma, A S Woods, R. J Cotter, E. V. Koonin, P. A Beachy, Cell 1996, 86, 21-34;
75. c) J. A. Porter, K. E Young, P A Beachy, Science 1996, 274, 255-259.
76. R K Mann, P A. Beachy, Biochim Biophys Acta 2000, 7529, 188-202
77. D Y. Jackson, J Burnier, C. Quan, M Stanley, J Tom, J A Wells, Science 1994, 266, 243-247
78. a) N. Wehofsky, N. Koglin, S. Thust, F Bordusa, J Am Chem Soc. 2003, 125, 6126-6133,
79. b) F Bordusa, Chem Rev. 2002, 702, 4817-4867.
80. J Phan, A. Zdanov, A. G. Evdokimov, J. E Tropea, H. K. Peters III, R B Kapust, M Li, A. Wlodawer, D S Waugh, J. Biol. Chem 2002, 277, 50564-50572
81. S. K. Mazmanian, G Liu, H. Ton-That, O Schneewind, Science 1999, 285, 760-763.
82. H Mao, S A Hart, A Schink, B A Pollok, J Am Chem Soc 2004, 726, 2670-2671