Staudinger-phosphonite reactions for the chemoselective transformation of azido-containing peptides and proteins

Organic Letters

Volumn 13, Issue 20, 2011, Pages 5440-5443

  Vallée, M Robert J ^a   Majkut, Paul ^a   Wilkening, Ina ^a   Weise, Christoph ^a   Müller, Gregor ^a   Hackenberger, Christian P R ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AZIDE; CALMODULIN; ORGANOPHOSPHORUS COMPOUND; PEPTIDE; PROTEIN; WATER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; SOLUBILITY;

AZIDES; CALMODULIN; COMBINATORIAL CHEMISTRY TECHNIQUES; MOLECULAR STRUCTURE; ORGANOPHOSPHORUS COMPOUNDS; PEPTIDES; PROTEINS; SOLUBILITY; WATER;

EID: 80054686497     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2020175     Document Type: Article

References (37)

1. Gaich, T.; Baran, P. S. J. Org. Chem. 2010, 75, 4657-4673
2. Young, I. S.; Baran, P. S. Nat. Chem. 2009, 1, 193-205
3. Hoffmann, R. W. Synthesis 2006, 21, 3531-3541
4. Hackenberger, C. P. R.; Schwarzer, D. Angew. Chem., Int. Ed. 2008, 47, 10030-10074
5. Sletten, E. M.; Bertozzi, C. R. Angew. Chem., Int. Ed. 2009, 48, 6974-6998
6. Prescher, J. A. Nat. Chem. Biol. 2005, 1, 13-21
7. Jessani, N.; Cravatt, B. F. Curr. Opin. Chem. Biol. 2004, 8, 54-59
8. Wang, L.; Schultz, P. G. Angew. Chem. 2005, 117, 34-68
9. Budisa, N. Angew. Chem. 2004, 116, 6586-6624
10. Angew. Chem., Int. Ed. 2004, 43, 6426-6463.
11. Link, A. J.; Mock, M. L.; Tirrell, D. A. Curr. Opin. Biotechnol. 2003, 14, 603-609
12. Dougherty, D. A. Curr. Opin. Chem. Biol. 2000, 4, 645-652
13. Davis, B. G. Pure Appl. Chem. 2009, 81, 285-298
14. Lavis, L. D.; Raines, R. T. ACS Chem. Biol. 2008, 3, 142-155
15. Mamidyala, S. K.; Finn, M. G. Chem. Soc. Rev. 2010, 39, 1252-1261
16. Finn, M. G.; Fokin, V. V. Chem. Soc. Rev. 2010, 39, 1231-1232
17. Jewett, J, C.; Bertozzi, C. R. Chem. Soc. Rev. 2010, 39, 1272-1279
18. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596-2599
19. Tornoe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057-3064
20. For seminal contributions, see: Huisgen, R.; Szeimies, G.; Moebius, L. Chem. Ber. 1967, 100, 2494-2507
21. Ning, X. H.; Guo, J.; Wolfert, M. A.; Boons, G. J. Angew. Chem. 2008, 120, 2285-2287
22. Angew. Chem., Int. Ed. 2008, 47, 2253-2255.
23. Agard, N. J.; Prescher, J. A.; Bertozzi, C. R. J. Am. Chem. Soc. 2004, 126, 15046-15047
24. Prescher, J. A.; Dube, D. H.; Bertozzi, C. R. Nature 2004, 430, 873-877
25. Hong, V.; Steinmetz, N. F.; Manchester, M.; Finn, M. G. Bioconjugate Chem. 2010, 21, 1912-1916
26. Laughlin, S. T.; Baskin, J. M.; Amacher, S. L.; Bertozzi, C. R. Science 2008, 320, 664-667
27. Serwa, R.; Wilkening, I.; del Signore, G.; Mühlberg, M.; Claußnitzer, I.; Weise, C.; Gerrits, M.; Hackenberger, C. P. R. Angew. Chem., Int. Ed. 2009, 48, 8234-8239
28. Boehrsch, V.; Serwa, R.; Majkut, P.; Krause, E.; Hackenberger, C. P. R. Chem. Commun. 2010, 46, 3176-3178
29. Gololobov, Y. G.; Zhmurova, I. N.; Kasukhin, L. F. Tetrahedron 1981, 37, 437-472
30. Koehn, M.; Breinbauer, R. Angew. Chem., Int. Ed. 2004, 43, 3106-3116
31. Schilling, C. I.; Jung, N.; Biskup, M.; Schepers, U.; Bräse, S. Chem. Soc. Rev. 2011, 40, 4840-4871
32. Mastryukova, T. A.; Mashckenko, N. V.; Odinets, I. L.; Petrovskii, P. V. Zhurnal Obshchei Khimii 1987, 58, 1967-1973
33. Malenko, D M.; Kasukhin, L. F.; Ponomarchuk, M. P.; Gololobov, Yu. G. Zhurnal Obshchei Khimii 1979, 50, 1950-1957
34. Wilkening, I.; del Signore, G.; Hackenberger, C. P. R. Chem. Commun. 2011, 47, 349-351
35. For a related report on the stabilty and water solubility of phosphites, see: Serwa, R.; Majkut, P.; Horstmann, B.; Swiecicki, J.-M.; Gerrits, M.; Krause, E.; Hackenberger, C. P. R. Chem. Sci. 2010, 1, 596-602
36. Haribabu, B.; Hook, S. S.; Selbert, M. A.; Goldstein, E. G.; Tomhave, E. D.; Edelman, A. M.; Snyderman, R.; Means, A. R. EMBO J. 1995, 14, 3679-86
37. Gerrits, M.; Strey, J.; Claußnitzer, I.; von Groll, U.; Schäfer, F.; Rimmele, M.; Stiege, W. Cell-free Synthesis of Defined Protein Conjugates by Site-directed Cotranslational Labeling. In Cell-free Expression; Kudlicki, T.; Katzen, F.; Bennett, R., Eds.; Landes Bioscience: Austin, TX, 2007; pp 166-180.