Generation of site-specific and enzymatically stable conjugates of recombinant proteins with ubiquitin-like modifiers by the cu'-catalyzed azide-alkyne cycloaddition

ChemBioChem

Volumn 11, Issue 6, 2010, Pages 774-777

  Weikart, Nadine D ^a   Mootz, Henning D ^a  

^a TU DORTMUND UNIVERSITY   (Germany)

Author keywords

Bioorthogonal ligation; Click chemistry; Isopeptidases; Post translational modifications; Proteins; SUMO

Indexed keywords

ALKYNE DERIVATIVE; AZIDE; CUPROUS ION; RECOMBINANT PROTEIN; UBIQUITIN; UBIQUITIN LIKE MODIFIER; UNCLASSIFIED DRUG;

ARTICLE; CONJUGATION; CONTROLLED STUDY; CYCLOADDITION; ENZYME ACTIVE SITE; ENZYME MECHANISM; ENZYME STABILITY; FEASIBILITY STUDY; NONHUMAN; PRIORITY JOURNAL; SITE DIRECTED MUTAGENESIS;

ALKYNES; AZIDES; CATALYSIS; COPPER; HUMANS; PROTEIN PROCESSING, POST-TRANSLATIONAL; RECOMBINANT PROTEINS; SMALL UBIQUITIN-RELATED MODIFIER PROTEINS; UBIQUITIN;

EID: 77950671571     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.200900738     Document Type: Article

References (47)

1. M. Hochstrasser, Nature 2009, 458, 422.
2. R. Geiss-Friedlander, F. Melchior, Nat. Rev. Mol. Cell Biol. 2007, 8, 947.
3. R. T. Hay, Mol. Cell 2005, 18, 1.
4. H. D. Ulrich, Methods Mol. Biol. 2009, 497, 3.
5. A. D. Capili, C. D. Lima, Curr. Opin. Struct. Biol. 2007, 17, 726.
6. Conjugation to the N terminus has also been observed. See ref. [1].
7. J. R. Mullen, S. J. Brill, J. Biol. Chem. 2008, 283, 19912.
8. V. Lallemand-Breitenbach, M. Jeanne, S. Benhenda, R. Nasr, M. Lei, L. Peres, J. Zhou, J. Zhu, B. Raught, H. de The, Nat. Cell Biol. 2008, 10, 547.
9. H. D. Ulrich, Mol. Cell 2008, 32, 301.
10. I. Matic, M. van Hagen, J. Schimmel, B. Macek, S. C. Ogg, M. H. Tatham, R. T. Hay, A. I. Lamond, M. Mann, A. C. O. Vertegaal, Mol. Cell Proteomics 2008, 7, 132.
11. D. Komander, Biochem. Soc. Trans 2009, 37, 937.
12. L Yin, B. Krantz, N. S. Russell, S. Deshpande, K. D. Wilkinson, Biochem-istry 2000, 39, 10001.
13. N. S. Russell, K. D. Wilkinson, Biochemistry 2004, 43, 4844.
14. J. E. Jung, H. P. Wollscheid, A. Marquardt, M. Manea, M. Scheffner, M. Przybylski, Bioconjug. Chem. 2009, 20, 1152.
15. T.W. Muir, D. Sondhi, P.A. Cole, Proc. Natl. Acad. Sci. USA 1998, 95, 6705.
16. T. C. Evans, Jr., J. Benner, M. Q. Xu, Protein Sci. 1998, 7, 2256.
17. K. S. Ajish Kumar, M. Haj-Yahya, D. Olschewski, H. A. Lashuel, A. Brik, Angew. Chem. 2009, 121, 8234;
18. Angew. Chem. Int. Ed. 2009, 48, 8090.
19. R. K. McGinty, J. Kim, C. Chatterjee, R. G. Roeder, T W. Muir, Nature 2008, 453, 812.
20. R. K. McGinty, M. Kohn, C. Chatterjee, K. P. Chiang, M. R. Pratt, T. W. Muir, ACS Chem. Biol. 2009, 4, 958.
21. R. Yang, K. K. Pasunooti, F. Li, X. W. Liu, C. F. Liu, J. Am. Chem. Soc. 2009, 131, 13592.
22. C. Chatterjee, R. K. McGinty, J. P. Pellois, T. W. Muir, Angew. Chem. 2007, 119, 2872;
23. Angew. Chem. Int. Ed. 2007, 46, 2814.
24. X. Li, T. Fekner, J. J. Ottesen, M. K. Chan, Angew. Chem. 2009, 121, 9348;
25. Angew. Chem. Int. Ed. 2009, 48, 9184.
26. V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem. 2002, 114, 2708;
27. Angew. Chem. Int. Ed. 2002, 41, 2596.
28. C. W. Tornøe, C. Christensen, M. Meldal, J. Org. Chem. 2002, 67, 3057.
29. M. Meldal, C. W. Tornøe, Chem. Rev. 2008, 108, 2952.
30. N. J. Agard, J. M. Baskin, J. A. Prescher, A. Lo, C. R. Bertozzi, ACS Chem. Biol. 2006, 1, 644.
31. A. Brik, J. Alexandratos, Y. C. Lin, J. H. Elder, A. J. Olson, A. Wlodawer, D. S. Goodsell, C. H. Wong, ChemBioChem 2005, 6, 1167.
32. W. S. Horne, M. K. Yadav, C. D. Stout, M. R. Ghadiri, J. Am. Chem. Soc. 2004, 126, 15366.
33. V. D. Bock, H. Hiemstra, J. H. van Maarseveen, Eur. J. Org. Chem. 2006, 51.
34. G. C. Tron, T. Pirali, R. A. Billington, P. L. Canonico, G. Sorba, A. A. Genaz-zani, Med. Res. Rev. 2008, 28, 278.
35. J. M. Chalker, G. J. Bernardes, Y. A. Lin, B. G. Davis, Chem. Asian J. 2009, 4, 630.
36. G. T. Hermanson, Bioconjugate Techniques, 2nd rev. ed., Academic Press, London, 2008.
37. A. Borodovsky, H. Ovaa, N. Kolli, T. Gan-Erdene, K. D. Wilkinson, H. L. Ploegh, B. M. Kessler, Chem. Biol. 2002, 9, 1149.
38. J. Kalia, R. T. Raines, ChemBioChem. 2006, 7, 1375.
39. E. Meulmeester, F. Melchior, Nature 2008, 452, 709.
40. M. H. Tatham, E. Jaffray, O. A. Vaughan, J. M. Desterro, C. H. Botting, J. H. Naismith, R. T. Hay, J. Biol. Chem. 2001, 276, 35 368.
41. J. S. Andersen, I. Matic, A. C. Vertegaal, Methods Mol. Biol. 2009, 497,19.
42. G. Rosas-Acosta, W. K. Russell, A. Deyrieux, D. H. Russell, V. G. Wilson, Mol. Cell Proteomics 2005, 4, 56.
43. J. W. Chin, S. W. Santoro, A. B. Martin, D. S. King, L. Wang, P. G. Schultz, J. Am. Chem. Soc. 2002, 124, 9026.
44. K. L. Kiick, E. Saxon, D. A. Tirrell, C. R. Bertozzi, Proc. Natl. Acad. Sci. USA 2002, 99, 19.
45. A. Deiters, P. G. Schultz, Bioorg. Med. Chem. Lett. 2005, 15, 1521.
46. N. Budisa, Angew. Chem. 2004, 116, 6586;
47. Angew. Chem. Int. Ed. 2004, 43, 6426.