Site-specific incorporation of p-propargyloxyphenylalanine in a cell-free environment for direct protein-protein click conjugation

Bioconjugate Chemistry

Volumn 21, Issue 2, 2010, Pages 255-263

  Bundy, Bradley C ^a   Swartz, James R ^a,b  

^a Stanford University   (United States)

^b Department of Electrical and Computer Engineering   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; BIOSYNTHESIS; COPPER COMPOUNDS; HYDROCARBONS; SOLUBILITY;

ALKYNE GROUPS; CELL FREE PROTEIN SYNTHESIS; CELL-FREE; CELLULAR UPTAKE; HIGH SPECIFICITY; IN-VIVO; SITE-SPECIFIC; TYROSINE ANALOGUES; UNNATURAL AMINO ACIDS; WATER SOLUBILITIES;

PROTEINS;

4 AZIDOPHENYLALANINE; 4 PROPARGYLOXYPHENYLALANINE; ALKYNE; AZIDE; CUPROUS ION; DIHYDROFOLATE REDUCTASE; GREEN FLUORESCENT PROTEIN; PHENYLALANINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CELL FREE PROTEIN SYNTHESIS; CONJUGATION; CYCLOADDITION; NONHUMAN; PROTEIN SYNTHESIS; REACTION ANALYSIS; ULTRAVIOLET RADIATION;

EID: 77049113819     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc9002844     Document Type: Article

References (41)

1. Hess, G. (2008) Generic biologics. Chem. Eng. News 86, 34-35.
2. Hermanson, G. T. (2008) Bioconjugate techniques, 2nd ed., pp 745-1045, Academic Press, Boston.
3. Esser-Kahn, A. P., and Francis, M. B. (2008) Protein-crosslinked polymeric materials through site-selective bioconjugation. Angew. Chem., Int. Ed. Engl. 47, 3751-3754.
4. Antos, J. M., and Francis, M. B. (2006) Transition metal catalyzed methods for site-selective protein modification. Curr. Opin. Chem. Biol. 10, 253-262.
5. Hermanson, G. T. (1996) Bioconjugate Techniques, 1st ed., pp 6-8, Academic Press, San Diego.
6. Gilmore, J. M., Scheck, R. A., Esser-Kahn, A. P., Joshi, N. S., and Francis, M. B. (2006) N-terminal protein modification through a biomimetic transamination reaction. Angew. Chem., Int. Ed. Engl. 45, 5307-5311.
7. Strable, E., Prasuhn, D. E., Jr., Udit, A. K., Brown, S., Link, A. J., Ngo, J. T., Lander, G., Quispe, J., Potter, C. S., Carragher, B., Tirrell, D. A., and Finn, M. G. (2008) Unnatural amino acid incorporation into virus-like particles. Bioconjugate Chem. 19, 866-875.
8. Wang, L., Brock, A., Herberich, B., and Schultz, P. G. (2001) Expanding the genetic code of Escherichia coli. Science 292, 498-500.
9. Xie, J., and Schultz, P. G. (2006) A chemical toolkit for proteins--an expanded genetic code. Nat. Rev. Mol. Cell. Biol. 7, 775-782.
10. Chin, J. W., Cropp, T. A., Anderson, J. C., Mukherji, M., Zhang, Z., and Schultz, P. G. (2003) An expanded eukaryotic genetic code. Science 301, 964-967.
11. Liu, W., Brock, A., Chen, S., and Schultz, P. G. (2007) Genetic incorporation of unnatural amino acids into proteins in mammalian cells. Nat. Methods 4, 239-244.
12. Goerke, A. R., and Swartz, J. R. (2009) High-level cell-free synthesis yields of proteins containing site-specific non-natural amino acids. Biotechnol. Bioeng. 102, 400-416.
13. Wang, L., Xie, J., Deniz, A. A., and Schultz, P. G. (2003) Unnatural amino acid mutagenesis of green fluorescent protein. J. Org. Chem. 68, 174-176.
14. Ryu, Y., and Schultz, P. G. (2006) Efficient incorporation of unnatural amino acids into proteins in Escherichia coli. Nat. Methods 3, 263-265.
15. Iida, S., Asakura, N., Tabata, K., Okura, I., and Kamachi, T. (2006) Incorporation of unnatural amino acids into cytochrome c3 and specific viologen binding to the unnatural amino acid. ChemBioChem 7, 1853-1855.
16. Deiters, A., and Schultz, P. G. (2005) In vivo incorporation of an alkyne into proteins in Escherichia coli. Bioorg. Med. Chem. Lett. 15, 1521-1524.
17. Chen, S., Schultz, P. G., and Brock, A. (2007) An improved system for the generation and analysis of mutant proteins containing unnatural amino acids in Saccharomyces cereVisiae. J. Mol. Biol. 371, 112-122.
18. O'Neil, M. J., Heckelman, P. E., Koch, C. B., and Roman, K. J., Eds. (2006) The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals, 14th ed., Merck & Co., Inc., Whitehouse Station, N.J.
19. Wang, L., Zhang, Z., Brock, A., and Schultz, P. G. (2003) Addition of the keto functional group to the genetic code of Escherichia coli. Proc. Natl. Acad. Sci. U.S.A. 100, 56-61.
20. Chin, J. W., Santoro, S. W., Martin, A. B., King, D. S., Wang, L., and Schultz, P. G. (2002) Addition of p-azido-L-phenylalanine to the genetic code of Escherichia coli. J. Am. Chem. Soc. 124, 9026-9027.
21. Swartz, J. R., Jewett, M. C., and Woodrow, K. M. (2004) Cell-free protein synthesis with prokaryotic combined transcription-translation, in Recombinant gene expression: reviews and protocols (Balbas, P., and Lorence, A., Eds.) pp 169-182, Humana Press, Totowa, NJ.
22. Kent, K. P., Childs, W., and Boxer, S. G. (2008) Deconstructing green fluorescent protein. J. Am. Chem. Soc. 130, 9664-9665.
23. Deiters, A., Cropp, T. A., Mukherji, M., Chin, J. W., Anderson, J. C., and Schultz, P. G. (2003) Adding amino acids with novel reactivity to the genetic code of Saccharomyces cerevisiae. J. Am. Chem. Soc. 125, 11782-11783.
24. Zawada, J., and Swartz, J. (2005) Maintaining rapid growth in moderate-density Escherichia coli fermentations. Biotechnol. Bioeng. 89, 407-415.
25. Jewett, M. C., and Swartz, J. R. (2004) Mimicking the Escherichia coli cytoplasmic environment activates long-lived and efficient cell-free protein synthesis. Biotechnol. Bioeng. 86, 19-26.
26. Abramoff, M. D., Magelhaes, P. J., and Ram, S. J. (2004) Image processing with ImageJ. Biophoton. Int. 11, 36-42.
27. van Kasteren, S. I., Kramer, H. B., Jensen, H. H., Campbell, S. J., Kirkpatrick, J., Oldham, N. J., Anthony, D. C., and Davis, B. G. (2007) Expanding the diversity of chemical protein modification allows post-translational mimicry. Nature 446, 1105-1109.
28. Scriven, E. F. V. (1984) Azides and nitrenes: reactiVity and utility, Academic Press, Orlando, FL.
29. Voloshin, A. M., and Swartz, J. R. (2008) Large Scale Batch Reactions for Cell-free Protein Synthesis, in Cell-free Protein Synthesis: Methods and Protocols (Spirin, A. S., and Swartz, J. R., Eds.) pp 207-236, Wiley-VCH Verlag GmbH & Co., Weinheim.
30. Bundy, B. C., Franciszkowicz, M. J., and Swartz, J. R. (2008) Escherichia coli-based cell-free synthesis of virus-like particles. Biotechnol. Bioeng. 100, 28-37.
31. Bonnefond, L., Giege, R., and Rudinger-Thirion, J. (2005) Evolution of the tRNA(Tyr)/TyrRS aminoacylation systems. Biochimie 87, 873-883.
32. Boonyaratanakornkit, B. B., Simpson, A. J., Whitehead, T. A., Fraser, C. M., El-Sayed, N. M., and Clark, D. S. (2005) Transcriptional profiling of the hyperthermophilic methanarchaeon Methanococcus jannaschii in response to lethal heat and non-lethal cold shock. Environ. Microbiol. 7, 789-797.
33. Underwood, K. A., Swartz, J. R., and Puglisi, J. D. (2005) Quantitative polysome analysis identifies limitations in bacterial cell-free protein synthesis. Biotechnol. Bioeng. 91, 425-435.
34. Kolb, H. C., Finn, M. G., and Sharpless, K. B. (2001) Click chemistry: diverse chemical function from a few good reactions. Angew. Chem. Int. Ed. Engl. 40, 2004-2021.
35. Tornoe, C. W., Christensen, C., and Meldal, M. (2002) Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. J. Org. Chem. 67, 3057-3064
36. Hong, V., Udit, A. K., Evans, R. A., and Finn, M. G. (2008) Electrochemically protected copper(I)-catalyzed azide-alkyne cycloaddition. ChemBioChem 9, 1481-1486.
37. Lutz, J. F. (2008) Copper-free azide-alkyne cycloadditions: new insights and perspectives. Angew. Chem., Int. Ed. Engl. 47, 2182-2184.
38. Link, A. J., and Tirrell, D. A. (2003) Cell surface labeling of Escherichia coli via copper(I)-catalyzed [3 + 2] cycloaddition. J. Am. Chem. Soc. 125, 11164-11165.
39. Jung, K., Park, J., Maeng, P. J., and Kim, H. (2005) Fluorescence quenching of green fluorescent protein. Bull. Korean Chem. Soc. 26, 413-417.
40. Prescher, J. A., and Bertozzi, C. R. (2005) Chemistry in living systems. Nat. Chem. Biol. 1, 13-21.
41. Baskin, J. M., Prescher, J. A., Laughlin, S. T., Agard, N. J., Chang, P. V., Miller, I. A., Lo, A., Codelli, J. A., and Bertozzi, C. R. (2007) Copper-free click chemistry for dynamic in vivo imaging. Proc. Natl. Acad. Sci. U.S.A. 104, 16793-16797.