Adding amino acids with novel reactivity to the genetic code of Saccharomyces cerevisiae

Journal of the American Chemical Society

Volumn 125, Issue 39, 2003, Pages 11782-11783

  Deiters, Alexander ^a   Cropp, T Ashton ^a   Mukherji, Mridul ^a   Chin, Jason W ^a   Anderson, J Christopher ^a   Schultz, Peter G ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID METABOLISM; ARTICLE; COVALENT BOND; CROSS LINKING; DERIVATIZATION; ENZYME SPECIFICITY; GENETIC CODE; METHODOLOGY; REACTION ANALYSIS; RESIDUE ANALYSIS; SACCHAROMYCES CEREVISIAE; STOP CODON;

ACETYLENE; AMINO ACIDS; AMINO ACYL-TRNA SYNTHETASES; AZIDES; CODON, NONSENSE; HUMANS; PROTEIN ENGINEERING; RNA, TRANSFER, AMINO ACID-SPECIFIC; SACCHAROMYCES CEREVISIAE; SUPEROXIDE DISMUTASE;

EID: 0141732270     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0370037     Document Type: Article

References (23)

1. Review: Lemineux, G. A.; Bertozzi, C. R. TIBTECH 1996, 16, 506-513.
2. (a) Cornish, V. W.; Hahn, K. M.; Schultz, P. G. J. Am. Chem. Soc. 1996, 118, 8150-8151.
3. (b) Mahal, L. K.; Yarema, K. J.; Bertozzi, C. R. Science 1997, 276, 1125-1128.
4. (a) Wang, L.; Brock, A.; Herberich, B.; Schultz, P. G. Science 2001, 292, 498-500.
5. (b) Chin, J. W.; Santoro, S. W.; Martin, A. B.; King, D. S.; Wang, L.; Schultz, P. G. J. Am. Chem. Soc. 2002, 124, 9026-9027.
6. (c) Chin, J. W.; Martin, A. B.; King, D. S.; Wang, L.; Schultz, P. G. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 11020-11024.
7. (a) Wang, L.; Zhang, Z.; Brock, A.; Schultz, P. G. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 56-61.
8. (b) Zhang, Z.; Smith, B. A.; Wang, L.; Brock, A.; Cho, C.; Schultz, P. G. Biochemistry 2003, 42, 6735-6746.
9. (c) Chin, J. W.; Cropp, T. A.; Anderson, J. C.; Mukherji, M.; Zhang, Z.; Schultz, P. G. Science, in press.
10. Reviews: (a) Padwa, A. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, U.K., 1991; Vol. 4, pp 1069-1109.
11. Huisgen, R. In 1,3-Dipolar Cycloaddition Chemistry, Padwa, A., Ed.; Wiley: New York, 1984; pp 1-176.
12. Another method is the ligand exchange on a bis-arsenic compound with a tetracysteine motif: Griffin, B. A.; Adams, S. R.; Tsien, R. Y. Science 1998, 281, 269-272.
13. (a) Tornoe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057-3064.
14. (b) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596-2599.
15. Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192-3193.
16. For another recent example of the electrophilic introduction of an azido group into a protein and a subsequent [3 + 2] cycloaddition see: Speers, A. E.; Adam, G. C.; Cravatt, B. F. J. Am. Chem. Soc. 2003, 125, 4686-4687.
17. Chin, J. W.; Cropp, T. A.; Chu, S.; Meggers, E.; Schultz, P. G. Chem. Biol. 2003, 10, 511-519.
18. (a) Keegan, L.; Gill, G.; Ptashne, M. Science 1986, 231, 699-704.
19. (b) Ptashne, M. Nature 1988, 335, 683-689.
20. (a) Blake, R. A. Curr. Opin. Pharmacol. 2001, 1, 533-539.
21. (b) Wouters, F. S.; Verveer, P. J.; Bastiaens, P. I. H. Trends Cell Biol. 2001, 11, 203-211.
22. (c) Zacharias, D. A.; Baird, G. S.; Tsien, R. Y. Curr. Opin. Neurobiol. 2000, 10, 416-421.
23. 495 values for SOD labeled with 5 or 6.