Extensive reprogramming of the genetic code for genetically encoded synthesis of highly N-alkylated polycyclic peptidomimetics

Journal of the American Chemical Society

Volumn 135, Issue 33, 2013, Pages 12297-12304

  Kawakami, Takashi ^a   Ishizawa, Takahiro ^a   Murakami, Hiroshi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BUILDING BLOCKES; CONFORMATIONAL RIGIDITY; CYCLIC STRUCTURES; DRUG CANDIDATES; PEPTIDE BACKBONES; PEPTIDOMIMETICS; PHARMACOLOGICAL PROPERTIES; PROTEOLYTIC STABILITY;

AMINO ACIDS;

PEPTIDES;

AMINO ACID; MESSENGER RNA; PEPTIDOMIMETIC AGENT;

ALKYLATION; AMINOACYLATION; ANTICODON; ARTICLE; CODON; DNA TEMPLATE; GENE SYNTHESIS; GENETIC CODE; IN VITRO SELECTION; NUCLEAR REPROGRAMMING; PEPTIDE LIBRARY; RIBOSOME;

ALKYLATION; BASE SEQUENCE; CODON; GENETIC ENGINEERING; MODELS, MOLECULAR; NUCLEIC ACID CONFORMATION; PEPTIDES, CYCLIC; PEPTIDOMIMETICS; RNA, CATALYTIC; RNA, TRANSFER; TRANSCRIPTION, GENETIC;

EID: 84883077144     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja405044k     Document Type: Article

References (57)

1. Mattheakis, L. C.; Bhatt, R. R.; Dower, W. J. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 9022
2. Hanes, J.; Pluckthun, A. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 4937
3. Nemoto, N.; MiyamotoSato, E.; Husimi, Y.; Yanagawa, H. FEBS Lett. 1997, 414, 405
4. Roberts, R. W.; Szostak, J. W. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 12297
5. Kawakami, T.; Murakami, H. J. Nucleic Acids 2012, 2012 713510
6. Hayashi, Y.; Morimoto, J.; Suga, H. ACS Chem. Biol. 2012, 7, 607
7. Morimoto, J.; Hayashi, Y.; Suga, H. Angew. Chem., Int. Ed. 2012, 51, 3423
8. Hofmann, F. T.; Szostak, J. W.; Seebeck, F. P. J. Am. Chem. Soc. 2012, 134, 8038
9. Schlippe, Y. V.; Hartman, M. C.; Josephson, K.; Szostak, J. W. J. Am. Chem. Soc. 2012, 134, 10469
10. Kwon, Y. U.; Kodadek, T. J. Am. Chem. Soc. 2007, 129, 1508
11. Chatterjee, J.; Gilon, C.; Hoffman, A.; Kessler, H. Acc. Chem. Res. 2008, 41, 1331
12. Tan, N. C.; Yu, P.; Kwon, Y. U.; Kodadek, T. Bioorg. Med. Chem. 2008, 16, 5853
13. White, T. R.; Renzelman, C. M.; Rand, A. C.; Rezai, T.; McEwen, C. M.; Gelev, V. M.; Turner, R. A.; Linington, R. G.; Leung, S. S.; Kalgutkar, A. S.; Bauman, J. N.; Zhang, Y.; Liras, S.; Price, D. A.; Mathiowetz, A. M.; Jacobson, M. P.; Lokey, R. S. Nat. Chem. Biol. 2011, 7, 810
14. Baeriswyl, V.; Heinis, C. Protein Eng. Des. Sel. 2013, 26, 81
15. Merryman, C.; Green, R. Chem. Biol. 2004, 11, 575
16. Tan, Z.; Forster, A. C.; Blacklow, S. C.; Cornish, V. W. J. Am. Chem. Soc. 2004, 126, 12752
17. Zhang, B.; Tan, Z.; Dickson, L. G.; Nalam, M. N.; Cornish, V. W.; Forster, A. C. J. Am. Chem. Soc. 2007, 129, 11316
18. Kawakami, T.; Murakami, H.; Suga, H. Chem. Biol. 2008, 15, 32
19. Kawakami, T.; Murakami, H.; Suga, H. J. Am. Chem. Soc. 2008, 130, 16861
20. Subtelny, A. O.; Hartman, M. C.; Szostak, J. W. J. Am. Chem. Soc. 2008, 130, 6131
21. Kawakami, T.; Ohta, A.; Ohuchi, M.; Ashigai, H.; Murakami, H.; Suga, H. Nat. Chem. Biol. 2009, 5, 888
22. Subtelny, A. O.; Hartman, M. C.; Szostak, J. W. Angew. Chem., Int. Ed. 2012, 50, 3164
23. Yamagishi, Y.; Shoji, I.; Miyagawa, S.; Kawakami, T.; Katoh, T.; Goto, Y.; Suga, H. Chem. Biol. 2011, 18, 1562
24. Kawakami, T.; Ishizawa, T.; Fujino, T.; Reid, P. C.; Suga, H.; Murakami, H. ACS Chem. Biol. 2013, 8, 1205
25. Cornish, V. W.; Mendel, D.; Schultz, P. G. Angew. Chem., Int. Ed. 1995, 34, 621
26. Deming, T. J. F., M. J.; Mason, T. L.; Tirrell, D. A. Macromolecules 1996, 29, 1442
27. Deming, T. J.; Fournier, M. J.; Mason, T. L.; Tirrell, D. A. J. Macromol. Sci. A: Pure Appl. Chem. 1997, 34, 2143
28. Steiner, T.; Hess, P.; Bae, J. H.; Wiltschi, B.; Moroder, L.; Budisa, N. PLoS One 2008, 3 e1680
29. Forster, A. C.; Tan, Z.; Nalam, M. N.; Lin, H.; Qu, H.; Cornish, V. W.; Blacklow, S. C. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 6353
30. Josephson, K.; Hartman, M. C. T.; Szostak, J. W. J. Am. Chem. Soc. 2005, 127, 11727
31. Murakami, H.; Ohta, A.; Ashigai, H.; Suga, H. Nat. Methods 2006, 3, 357
32. Forster, A. C.; Weissbach, H.; Blacklow, S. C. Anal. Biochem. 2001, 297, 60
33. Shimizu, Y.; Inoue, A.; Tomari, Y.; Suzuki, T.; Yokogawa, T.; Nishikawa, K.; Ueda, T. Nat. Biotechnol. 2001, 19, 751
34. Hartman, M. C.; Josephson, K.; Lin, C. W.; Szostak, J. W. PLoS One 2007, 2 e972
35. Ohta, A.; Murakami, H.; Higashimura, E.; Suga, H. Chem Biol 2007, 14, 1315
36. Forster, A. C. Nucleic Acids Res. 2009, 37, 3747
37. Forster, A. C. Biotechnol. J. 2012, 7, 835
38. Heckler, T. G.; Chang, L. H.; Zama, Y.; Naka, T.; Chorghade, M. S.; Hecht, S. M. Biochemistry 1984, 23, 1468
39. Hartman, M. C.; Josephson, K.; Szostak, J. W. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 4356
40. Ohuchi, M.; Murakami, H.; Suga, H. Curr. Opin. Chem. Biol. 2007, 11, 537
41. Xiao, H.; Murakami, H.; Suga, H.; Ferre-D'Amare, A. R. Nature 2008, 454, 358
42. Niwa, N.; Yamagishi, Y.; Murakami, H.; Suga, H. Bioorg. Med. Chem. Lett. 2009, 19, 3892
43. Ishizawa, T.; Kawakami, T.; Reid, P. C.; Murakami, H. J. Am. Chem. Soc. 2013, 135, 5433
44. Karginov, V. A.; Mamaev, S. V.; An, H.; Van Cleve, M.; Hecht, S. M.; Komatsoulis, G. A.; Abelson, J. N. J. Am. Chem. Soc. 1997, 119, 8166
45. Choudhury, A. K.; Golovine, S. Y.; Dedkova, L. M.; Hecht, S. M. Biochemistry 2007, 46, 4066
46. Kane, J. F.; Violand, B. N.; Curran, D. F.; Staten, N. R.; Duffin, K. L.; Bogosian, G. Nucleic Acids Res. 1992, 20, 6707
47. Fujino, T.; Goto, Y.; Suga, H.; Murakami, H. J. Am. Chem. Soc. 2013, 135, 1830
48. Cochella, L.; Green, R. Science 2005, 308, 1178
49. Johansson, M.; Lovmar, M.; Ehrenberg, M. Curr. Opin. Microbiol. 2008, 11, 141
50. Ledoux, S.; Olejniczak, M.; Uhlenbeck, O. C. Nat. Struct. Mol. Biol. 2009, 16, 359
51. Murakami, H.; Ohta, A.; Suga, H. Nat. Struct. Mol. Biol. 2009, 16, 353
52. Zaher, H. S.; Green, R. Cell 2009, 136, 746
53. Wohlgemuth, I.; Brenner, S.; Beringer, M.; Rodnina, M. V. J. Biol. Chem. 2008, 283, 32229
54. Pavlov, M. Y.; Watts, R. E.; Tan, Z.; Cornish, V. W.; Ehrenberg, M.; Forster, A. C. Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 50
55. Doerfel, L. K.; Wohlgemuth, I.; Kothe, C.; Peske, F.; Urlaub, H.; Rodnina, M. V. Science 2013, 339, 85
56. Ude, S.; Lassak, J.; Starosta, A. L.; Kraxenberger, T.; Wilson, D. N.; Jung, K. Science 2013, 339, 82
57. Kawakami, T.; Cheng, H.; Hashiro, S.; Nomura, Y.; Tsukiji, S.; Furuta, T.; Nagamune, T. ChemBioChem 2008, 9, 1583