Facile conversion of cysteine and alkyl cysteines to dehydroalanine on protein surfaces: Versatile and switchable access to functionalized proteins

Journal of the American Chemical Society

Volumn 130, Issue 15, 2008, Pages 5052-5053

  Bernardes, Gonçalo J L ^a   Chalker, Justin M ^a   Errey, James C ^a   Davis, Benjamin G ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; CYSTEINE DERIVATIVE; DEHYDROALANINE;

ARTICLE; BIOTRANSFORMATION; DIASTEREOISOMER; ELIMINATION REACTION; OXIDATION; PROTEIN PROCESSING; PROTEIN PROTEIN INTERACTION; PROTEIN STRUCTURE; SYNTHESIS;

ALANINE; ALKYLATION; CYSTEINE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PROTEIN PROCESSING, POST-TRANSLATIONAL; PROTEINS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SURFACE PROPERTIES;

EID: 42149123238     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja800800p     Document Type: Article

References (34)

1. (a) Davis, B. G. Science 2004, 303, 480-482.
2. (b) van Kasteren, S. I.; Kramer, H. B.; Jensen, H. H.; Campbell, S. J.; Kirkpatrick, J.; Oldham, N. J.; Anthony, D. C.; Davis, B. G. Nature 2007, 446, 1105-1109.
3. (c) Foley, T. L.; Burkart, M. D. Curr. Opin. Chem. Biol. 2007, 11, 12-19.
4. Rich, D. H.; Mathiaparanam, T. P.; Grant, J. A.; Mabuni, C. J. Chem. Soc., Chem. Commun. 1974, 897-898.
5. (a) Hashimoto, K.; Sakai, M.; Okuno, T.; Shirahama, H. Chem. Commun. 1996, 1139-1140.
6. (b) Okeley, N.; Zhu, Y.; van der Donk, W. A. Org. Lett. 2000, 2, 3603-3606.
7. Seebeck, F. P.; Szostak, J. W J. Am. Chem. Soc. 2006, 128, 7150-7151.
8. Wang, J.; Schiller, S. M.; Schultz, P. G. Angew. Chem., Int. Ed. 2007, 46, 6849-6851.
9. Holmes, T. J., Jr.; Lawton, R. G. J. Am. Chem. Soc. 1977, 99, 1984-1986.
10. (a) Tamura, Y.; Minamikawa, J.; Sumoto, K.; Fujii, S.; Ikeda, M. J. Org. Chem. 1973, 38, 1239-1241.
11. (b) Johnson, C. R.; Kirchhoff, R. A.; Corkins, H. G. J. Org. Chem. 1974, 39, 2458-2459.
12. (a) Franek, W.; Claus, P. K. Monatsh. Chem. 1990, 121, 539-547.
13. (b) Matsuo, J.; Kozai, T.; Ishibashi, H. Org. Lett. 2006, 8, 6095-6098.
14. Furukawa, N.; Omata, T.; Yoshimura, T.; Aida, T.; Oae, S. Tetrahedron Lett. 1972, 16, 1619-1622.
15. See Supporting Information for full details.
16. For sulfilimine conversion to sulfides and sulfoxides, see refs 8b and 9.
17. DeSantis, G.; Berglund, P.; Stabile, M. R.; Gold, M.; Jones, J. B. Biochemistry 1998, 37, 5968-5973.
18. In addition to the selective Met recovery shown in Scheme 1, differential accessibility of C156, M119, M175, and M222 may also play a role.
19. (a) Hunter, T.; Karin, M. Cell 1992, 70, 375-387.
20. (b) Cohen, P. Nat. Cell Biol. 2002, 4, E127-E130.
21. (a) Dwek, R. A. Chem. Rev. 1996, 96, 683-720.
22. (b) Davis, B. G. Chem. Rev. 2002, 102, 579-601.
23. (c) Ohtsubo, K.; Marth, J. D. Cell 2006, 126, 855-867.
24. DeSantis, G.; Paech, C.; Jones, J. B. Bioorg. Med. Chem. 2000, 8, 563-570.
25. (a) Danishefsky, S. J.; Allen, J. A. Angew. Chem., Int. Ed. 2000, 39, 836-863.
26. (b) Ouerfelli, O.; Warren, J. D.; Wilson, R. M.; Danishefsky, S. J. Exp. Rev. Vaccines 2005, 4, 677-685.
27. (c) Wittrock, S.; Becker, T.; Kunz, H. Angew. Chem., Int. Ed. 2007, 46, 5226-5230.
28. Simon, M. D.; Chu, F.; Racki, L. R.; de la Cruz, C. C.; Burlingame, A. L.; Panning, B.; Narlikar, G. J.; Shokat, K. M. Cell 2007, 128, 1003-1012.
29. Trojer, P.; Reinberg, D. Cell 2006, 125, 213-217.
30. (a) Zhang, F. L.; Casey, P. J. Annu. Rev. Biochem. 1996, 65, 241-269.
31. (b) Marshall, C. J. Science 1993, 259, 1865-1866.
32. (a) Zhu, Y.; van der Donk, W. A. Org. Lett. 2001, 3, 1189-1192.
33. (b) Galonic, D. P.; van der Donk, W. A.; Gin, D. Y. Chem. - Eur. J. 2003, 9, 5997-6006.
34. Schmidt, U.; Öhler, E. Angew. Chem., Int. Ed. Engl. 1976, 15, 42.