In situ deprotection and incorporation of unnatural amino acids during cell-free protein synthesis

Chemistry - A European Journal

Volumn 19, Issue 21, 2013, Pages 6824-6830

  Arthur, Isaac N ^a   Hennessy, James E ^a   Padmakshan, Dharshana ^a   Stigers, Dannon J ^a   Lesturgez, Stéphanie ^a   Fraser, Samuel A ^a   Liutkus, Mantas ^a   Otting, Gottfried ^a   Oakeshott, John G ^b   Easton, Christopher J ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

^b CSIRO   (Australia)

Author keywords

amino acids; cell free synthesis; enzyme catalysis; protecting groups; protein expression

Indexed keywords

CELL FREE PROTEIN SYNTHESIS; CELL-FREE; ENZYME CATALYSIS; FREE AMINO ACIDS; PROTECTING GROUP; PROTEIN EXPRESSIONS; STANDARD CONDITIONS; UNNATURAL AMINO ACIDS;

AMINO ACIDS; ESCHERICHIA COLI; ESTERIFICATION; ESTERS; MACHINERY; PROTEINS;

BIOSYNTHESIS;

AMINO ACID; ESTER;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; ESCHERICHIA COLI; METABOLISM; PROTEIN SYNTHESIS;

AMINO ACIDS; CATALYSIS; ESCHERICHIA COLI; ESTERS; MOLECULAR STRUCTURE; PROTEIN BIOSYNTHESIS;

EID: 84877778114     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201203923     Document Type: Article

References (53)

1. A. S. Spirin, V. I. Baranov, L. A. Ryabova, S. Y. Ovodov, Y. B. Alakhov, Science 1988, 242, 1162-1164.
2. T. Kigawa, T. Yabuki, Y. Yoshida, M. Tsutsui, Y. Ito, T. Shibata, S. Yokoyama, FEBS Lett. 1999, 442, 15-19.
3. J. R. Swartz, M. C. Jewett, K. A. Woodrow in Methods in Molecular Biology, Vol. 267: Recombinant Gene Expression, 2nd ed. (Eds.: P. Balbs, A. Lorence), Humana Press Inc., Totowa, NJ, 2004, pp. 169-182.
4. M. Ohuchi, H. Murakami, H. Suga, Curr. Opin. Chem. Biol. 2007, 11, 537-542.
5. Y. Shimizu, T. Ueda in Methods in Molecular Biology, Vol. 607: Cell-Free Protein Production, 1st ed. (Eds.: Y. Endo, K. Takai, T. Ueda), Humana Press Inc., New York, NY, 2010, pp. 11-21.
6. T. Kigawa, E. Yamaguchi-Nunokawa, K. Kodama, T. Matsuda, T. Yabuki, N. Matsuda, R. Ishitani, O. Nureki, S. Yokoyama, J. Struct. Funct. Genomics 2002, 2, 29-35.
7. V. Bergo, S. Mamaev, J. Olejnik, K. J. Rothschild, Biophys. J. 2003, 84, 960-966.
8. K. Ozawa, M. J. Headlam, P. M. Schaeffer, B. R. Henderson, N. E. Dixon, G. Otting, Eur. J. Biochem. 2004, 271, 4084-4093.
9. F. Katzen, G. Chang, W. Kudlicki, Trends Biotechnol. 2005, 23, 150-156.
10. K. Ozawa, M. J. Headlam, D. Mouradov, S. J. Watt, J. L. Beck, K. J. Rodgers, R. T. Dean, T. Huber, G. Otting, N. E. Dixon, FEBS J. 2005, 272, 3162-3171.
11. D. J. Stigers, Z. I. Watts, J. E. Hennessy, H.-K. Kim, R. Martini, M. C. Taylor, K. Ozawa, J. W. Keillor, N. E. Dixon, C. J. Easton, Chem. Commun. 2011, 47, 1839-1841.
12. A. R. Goerke, J. R. Swartz, Biotechnol. Bioeng. 2009, 102, 400-416.
13. I. N. Ugwumba, K. Ozawa, Z.-Q. Xu, F. Ely, J.-L. Foo, A. J. Herlt, C. Coppin, S. Brown, M. C. Taylor, D. L. Ollis, L. N. Mander, G. Schenk, N. E. Dixon, G. Otting, J. G. Oakeshott, C. J. Jackson, J. Am. Chem. Soc. 2011, 133, 326-333.
14. K. V. Loscha, A. J. Herlt, R. Qi, T. Huber, K. Ozawa, G. Otting, Angew. Chem. 2012, 124, 2286-2289
15. Angew. Chem. Int. Ed. 2012, 51, 2243-2246.
16. T. L. Hendrickson, V. de Crcy-Lagard, P. Schimmel, Annu. Rev. Biochem. 2004, 73, 147-176.
17. B. Holzberger, M. Rubini, H. M. Mçller, A. Marx, Angew. Chem. 2010, 122, 1346-1349
18. Angew. Chem. Int. Ed. 2010, 49, 1324-1327.
19. C. C. Liu, P. G. Schultz, Annu. Rev. Biochem. 2010, 79, 413-444.
20. M. G. Hoesl, N. Budisa, Angew. Chem. 2011, 123, 2948-2955
21. Angew. Chem. Int. Ed. 2011, 50, 2896-2902.
22. A. Isidro-Llobet, M. Lvarez, F. Albericio, Chem. Rev. 2009, 109, 2455-2504.
23. D. Padmakshan, S. A. Bennett, G. Otting, C. J. Easton, Synlett 2007, 1083-1084.
24. L. Guignard, K. Ozawa, S. E. Pursglove, G. Otting, N. E. Dixon, FEBS Lett. 2002, 524, 159-162.
25. M. A. Apponyi, K. Ozawa, N. E. Dixon, G. Otting in Methods in Molecular Biology, Vol. 426: Structural Proteomics: High Throughput Methods, (Eds.: B. Kobe, M. Guss, T. Huber), Humana Press Inc., Totowa, NJ, 2008, pp. 257-268.
26. M. Schelhaas, H. Waldmann, Angew. Chem. 1996, 108, 2192-2219
27. Angew. Chem. Int. Ed. Engl. 1996, 35, 2056-2083.
28. J. F. Carson, Synthesis 1980, 730-733.
29. C. J. Easton, Chem. Rev. 1997, 97, 53-82.
30. A. K. Croft, C. J. Easton, L. Radom, J. Am. Chem. Soc. 2003, 125, 4119-4124.
31. A. K. Croft, C. J. Easton, K. Kociuba, L. Radom, Tetrahedron: Asymmetry 2003, 14, 2919-2926.
32. S. Fittkau, U. Fçrster, C. Pascual, W.-H. Schunck, Eur. J. Biochem. 1974, 44, 523-528.
33. C. Lazdunski, J. Busuttil, A. Lazdunski, Eur. J. Biochem. 1975, 60, 369.
34. F. C. Golich, M. Han, M. W. Crowder, Protein Expression Purif. 2006, 47, 634-639.
35. D. Chandu, D. Nandi, Microbiology 2003, 149, 3437-3447.
36. A. Ben-Bassat, K. Bauer, S. Y. Chang, K. Myambo, A. Boosman, S. Chang, J. Bacteriol. 1987, 169, 751-757.
37. Z. Mathew, T. M. Knox, C. G. Miller, J. Bacteriol. 2000, 182, 3383-3393.
38. T. Juhsz, Z. Szeltner, V. Renner, L. Polgr, Biochemistry 2002, 41, 4096-4106.
39. T. H. T. Coetzer, J. P. D. Goldring, L. E. J. Huson, Biochimie 2008, 90, 336-344.
40. E. E. Haley, J. Biol. Chem. 1968, 243, 5748-5752.
41. J. D. Gary, S. Clarke, J. Biol. Chem. 1995, 270, 4076-4087.
42. H. Suzuki, S. Izuka, H. Minami, N. Miyakawa, S. Ishihara, H. Kumagai, Appl. Environ. Microbiol. 2003, 69, 6399-6404.
43. H. Suzuki, H. Kumagai, T. Tochikura, J. Bacteriol. 1986, 168, 1325-1331.
44. S. Prusiner, R. E. Miller, R. C. Valentine, Proc. Natl. Acad. Sci. USA 1972, 69, 2922-2926.
45. C. J. Easton, C. A. Hutton, G. Rositano, E. W. Tan, J. Org. Chem. 1991, 56, 5614-5618.
46. C. J. Easton, C. A. Hutton, M. C. Merrett, E. R. T. Tiekink, Tetrahedron 1996, 52, 7025-7036.
47. Z. I. Watts, C. J. Easton, J. Am. Chem. Soc. 2009, 131, 11323-11325.
48. J. C. M. van Hest, D. A. Tirrell, Chem. Commun. 2001, 1897-1904.
49. G. Verardo, N. Toniutti, A. Gorassini, A. G. Giumanini, Eur. J. Org. Chem. 1999, 2943-2948.
50. R. E. Dawson, A. Hennig, D. P. Weimann, D. Emery, V. Ravikumar, J. Montenegro, T. Takeuchi, S. Gabutti, M. Mayor, J. Mareda, C. A. Schalley, S. Matile, Nat. Chem. 2010, 2, 533-538.
51. A. K. H. Hirsch, E. Buhler, J.-M. Lehn, J. Am. Chem. Soc. 2012, 134, 4177-4183.
52. S. M. Iossifidou, C. C. Froussios, Synthesis 1996, 1355-1358.
53. C. J. Easton, A. J. Edwards, S. B. McNabb, M. C. Merrett, J. L. OConnell, G. W. Simpson, J. S. Simpson, A. C. Willis, Org. Biomol. Chem. 2003, 1, 2492-2498.