The Staudinger ligation - A gift to chemical biology

Angewandte Chemie - International Edition

Volumn 43, Issue 24, 2004, Pages 3106-3116

  Köhn, Maja ^a,b   Breinbauer, Rolf ^a,b  

^a MAX PLANCK INSTITUTE OF MOLECULAR PHYSIOLOGY   (Germany)

^b TU DORTMUND UNIVERSITY   (Germany)

Author keywords

Bioconjugates; Bioorganic chemistry; Chemical biology; Peptides; Staudinger ligation

Indexed keywords

BIOCHEMISTRY; CHEMICAL ANALYSIS; SYNTHESIS (CHEMICAL);

CHEMOSELECTIVE LIGATION; STAUDINGER LIGATION;

ORGANIC COMPOUNDS;

AZIDE;

BIOLOGY; CELL ACTIVITY; CHEMICAL REACTION; CHEMICAL STRUCTURE; LIGATION; ORGANIC CHEMISTRY; SHORT SURVEY;

AZIDES; CHEMISTRY, ORGANIC; GENETIC ENGINEERING; HISTORY, 20TH CENTURY; LIGANDS; PEPTIDES; PHOSPHINES;

EID: 4344639697     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200401744     Document Type: Short Survey

References (44)

1. G. T. Hermanson, Bioconjugate Techniques, Academic Press, San Diego, 1996.
2. H. C. Hang, C. R. Bertozzi, Acc. Chem. Res. 2001, 34, 727-736.
3. a) W. G. Lewis, L. G. Green, F. Grynszpan, Z. Radic, P. R. Carlier, P. Taylor, M. G. Finn, K. B. Sharpless, Angew. Chem. 2002, 114, 1095-1099; Angew. Chem. Int. Ed. 2002, 41, 1053-1057;
4. a) W. G. Lewis, L. G. Green, F. Grynszpan, Z. Radic, P. R. Carlier, P. Taylor, M. G. Finn, K. B. Sharpless, Angew. Chem. 2002, 114, 1095-1099; Angew. Chem. Int. Ed. 2002, 41, 1053-1057;
5. b) V. V. Rostovtsev, L. G. Freen, V. V. Fokin, K. B. Sharpless, Angew. Chem. 2002, 114, 2708-2711; Angew. Chem. Int. Ed. 2002, 41, 2596-2599;
6. b) V. V. Rostovtsev, L. G. Freen, V. V. Fokin, K. B. Sharpless, Angew. Chem. 2002, 114, 2708-2711; Angew. Chem. Int. Ed. 2002, 41, 2596-2599;
7. c) C. W. Tornoe, C. Christensen, M. Meldal, J. Org. Chem. 2002, 67, 3057-3064;
8. d) F. Fazio, M. C. Bryan, O. Blixt, J. C. Paulson, C.-H. Wong, J. Am. Chem. Soc. 2002, 124, 14397-14402;
9. e) Q. Wang, T. R. Chan, R. Hilgraf, V. V. Fokin, K. B. Sharpless, M. G. Finn, J. Am. Chem. Soc. 2003, 125, 3192-3193;
10. f) R. Breinbauer, M. Köhn, ChemBioChem 2003, 4, 1147-1149.
11. E. Saxon, C. R. Bertozzi, Science 2000, 287, 2007-2010.
12. H. Staudinger, J. Meyer, Helv. Chim. Acta 1919, 2, 635-646.
13. For a comprehensive review, see: a) Y. G. Gololobov, I. N. Zhmurova, L. F. Kasukhin, Tetrahedron 1981, 37, 437-472;
14. b) Y. G. Gololobov, L. F. Kasukhin, Tetrahedron 1992, 48, 1353-1406.
15. P. M. Fresnada, P. Molina, Synlett 2004, 1-11.
16. H. Staudinger, E. Hauser, Helv. Chim. Acta 1921, 4, 861.
17. S. Luchansky, H. C. Hang, E. Saxon, J. R. Grunwell, C. Yu, D. H. Dube, C. R. Bertozzi, Methods Enzymol. 2003, 362, 249-272.
18. E. Saxon, S. Luchansky, H. C. Hang, C. Yu, S. C. Lee, C. R. Bertozzi, J. Am. Chem. Soc. 2002, 124, 14893-14902.
19. E. Saxon, J. I. Armstrong, C. R. Bertozzi, Org. Lett. 2000, 2, 2141-2143.
20. a) B. L. Nilsson, L. L. Kiessling, R. T. Raines, Org. Lett. 2000, 2, 1939-1941;
21. b) B. L. Nilsson, L. L. Kiessling, R. T. Raines, Org. Lett. 2001, 3, 9-12;
22. c) M. B. Soellner, B. L. Nilsson, R. T. Raines, J. Org. Chem. 2002, 67, 4993-4996.
23. G. J. Cotton, T. W. Muir, Chem. Biol. 1999, 6, R247-R256.
24. a) T. Wieland, E. Bokelmann, L. Bauer, H. U. Lang, H. Lau, Justus Liebigs Ann. Chem. 1953, 583, 129-149;
25. b) P. E. Dawson, T. W. Muir, I. Clark-Lewis, S. B. H. Kent, Science 1994, 266, 776-779.
26. a) J. Zaloom, D. C. Roberts, J. Org. Chem. 1981, 46, 5173-5176;
27. b) J. T. Lundquist IV, J. C. Pelletier, Org. Lett. 2001, 3, 781-783;
28. c) P. T. Nyffeler, C.-H. Liang, K. M. Koeller, C.-H. Wong, J. Am. Chem. Soc. 2002, 124, 10773-10778.
29. For a comprehensive review on methods for the preparation of azides, see: E. F. V. Scriven, K. Turnbull, Chem. Rev. 1988, 88, 297-368.
30. B. L. Nilsson, R. J. Hondal, M. B. Soellner, R. T. Raines, J. Am. Chem. Soc. 2003, 125, 5268-5269.
31. R. Merkx, D. T. S. Rijkers, J. Kemmink, R. M. J. Liskamp, Tetrahedron Lett. 2003, 44, 4515-4518.
32. O. David, W. J. N. Meester, H. Bieräugel, H. E. Schoemaker, H. Hiemstra, J. H. van Maarseveen, Angew. Chem. 2003, 115, 4509-4511; Angew. Chem. Int. Ed. 2003, 42, 4373-4375.
33. O. David, W. J. N. Meester, H. Bieräugel, H. E. Schoemaker, H. Hiemstra, J. H. van Maarseveen, Angew. Chem. 2003, 115, 4509-4511; Angew. Chem. Int. Ed. 2003, 42, 4373-4375.
34. K. L. Kiick, E. Saxon, D. A. Tirrell, C. R. Bertozzi, Proc. Natl. Acad. Sci. USA 2002, 99, 19-24.
35. G. A. Lemieux, C. L. de Graffenried, C. R. Bertozzi, J. Am. Chem. Soc. 2003, 125, 4708-4709.
36. C. C.-Y. Wang, T. S. Seo, Z. Li, H. Ruparel, J. Ju, Bioconjugate Chem. 2003, 14, 697-701.
37. A. E. Speers, B. F. Cravatt, ChemBioChem 2004, 5, 41-47.
38. H. Ovaa, P. F. van Swieten, B. M. Kessler, M. A. Leeuwenburgh, E. Fiebiger, A. M. C. H. van den Nieuwendijk, P. J. Galardy, G. A. van der Marel, H. L. Ploegh, H. S. Overkleeft, Angew. Chem. 2003, 115, 3754-3757; Angew. Chem. Int. Ed. 2003, 42, 3626-3629.
39. H. Ovaa, P. F. van Swieten, B. M. Kessler, M. A. Leeuwenburgh, E. Fiebiger, A. M. C. H. van den Nieuwendijk, P. J. Galardy, G. A. van der Marel, H. L. Ploegh, H. S. Overkleeft, Angew. Chem. 2003, 115, 3754-3757; Angew. Chem. Int. Ed. 2003, 42, 3626-3629.
40. H. C. Hang, C. Yu, D. L. Kalo, C. R. Bertozzi, Proc. Natl. Acad. Sci. USA 2003, 100, 14846-14851.
41. H. C. Hang, C. Yu, M. R. Pratt, C. R. Bertozzi, J. Am. Chem. Soc. 2004, 126, 6-7.
42. M. B. Soellner, K. A. Dickson, B. L. Nilsson, R. T. Raines, J. Am. Chem. Soc. 2003, 125, 11790-11791.
43. M. Köhn, R. Wacker, C. Peters, H. Schröder, L. Soulere, R. Breinbauer, C. M. Niemeyer, H. Waldmann, Angew. Chem. 2003, 115, 6010-6014; Angew. Chem. Int. Ed. 2003, 42, 5830-5834.
44. M. Köhn, R. Wacker, C. Peters, H. Schröder, L. Soulere, R. Breinbauer, C. M. Niemeyer, H. Waldmann, Angew. Chem. 2003, 115, 6010-6014; Angew. Chem. Int. Ed. 2003, 42, 5830-5834.