Peptide ligation and RNA cleavage via an abiotic template interface

Journal of the American Chemical Society

Volumn 137, Issue 11, 2015, Pages 3751-3754

  Piao, Xijun ^a   Xia, Xin ^a   Mao, Jie ^a   Bong, Dennis ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOMOLECULES; DNA; PEPTIDES; RNA; TOPOLOGY;

CHAIN EXTENSION; CHEMICAL TRANSFORMATIONS; FACILE INSERTION; HYBRID INTERFACE; OXIDATIVE COUPLINGS; PEPTIDE LIGATIONS; PEPTIDE NUCLEIC ACID; REACTION SITES;

NUCLEIC ACIDS;

AMIDE; NUCLEIC ACID; PEPTIDE; PEPTIDE NUCLEIC ACID; RIBOZYME; RNA;

ARTICLE; BASE PAIRING; CATALYSIS; CHEMICAL BOND; DNA HAIRPIN; DNA HYBRIDIZATION; DNA STRAND; DNA TEMPLATE; HYBRIDIZATION; OXIDATIVE COUPLING; PROTEIN FOLDING; RNA CLEAVAGE; CONFORMATION; PHYSIOLOGY; PROTEIN CONFORMATION; SYNTHESIS;

NUCLEIC ACID CONFORMATION; PEPTIDES; PROTEIN CONFORMATION; RNA CLEAVAGE;

EID: 84925796368     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b00236     Document Type: Article

References (59)

1. Schmidt, J. G.; Nielsen, P. E.; Orgel, L. E. Nucleic Acids Res. 1997, 25, 4797
2. Schmidt, J. G.; Christensen, L.; Nielsen, P. E.; Orgel, L. E. Nucleic Acids Res. 1997, 25, 4792
3. Zhan, Z. Y. J.; Lynn, D. G. J. Am. Chem. Soc. 1997, 119, 12420
4. Goodwin, J. T.; Mehta, A. K.; Lynn, D. G. Acc. Chem. Res. 2012, 45, 2189
5. Nielsen, P. E. Acc. Chem. Res. 1999, 32, 624
6. Sharma, A. K.; Heemstra, J. M. J. Am. Chem. Soc. 2011, 133, 12426
7. Grossmann, T. N.; Seitz, O. J. Am. Chem. Soc. 2006, 128, 15596
8. McKee, M. L.; Milnes, P. J.; Bath, J.; Stulz, E.; Turberfield, A. J.; OReilly, R. K. Angew. Chem., Int. Ed. 2010, 49, 7948
9. McKee, M. L.; Evans, A. C.; Gerrard, S. R.; OReilly, R. K.; Turberfield, A. J.; Stulz, E. Org. Biomol. Chem. 2011, 9, 1661
10. Silverman, A. P.; Kool, E. T. Chem. Rev. 2006, 106, 3775
11. Kleiner, R. E.; Dumelin, C. E.; Liu, D. R. Chem. Soc. Rev. 2011, 40, 5707
12. Von Kiedrowski, G. Angew. Chem., Int. Ed. 1986, 25, 932
13. Li, Z. Y.; Zhang, Z. Y. J.; Knipe, R.; Lynn, D. G. J. Am. Chem. Soc. 2002, 124, 746
14. Rosenbaum, D. M.; Liu, D. R. J. Am. Chem. Soc. 2003, 125, 13924
15. Lo, P. K.; Sleiman, H. F. J. Am. Chem. Soc. 2009, 131, 4182
16. Ura, Y.; Beierle, J. M.; Leman, L. J.; Orgel, L. E.; Ghadiri, M. R. Science 2009, 325, 73
17. Heemstra, J. M.; Liu, D. R. J. Am. Chem. Soc. 2009, 131, 11347
18. McHale, R.; OReilly, R. K. Macromolecules 2012, 45, 7665
19. Zeng, Y.; Pratumyot, Y.; Piao, X.; Bong, D. J. Am. Chem. Soc. 2012, 134, 832
20. Piao, X.; Xia, X.; Bong, D. Biochemistry 2013, 52, 6313
21. Xia, X.; Piao, X.; Fredrick, K.; Bong, D. ChemBioChem 2013, 15, 31
22. Xia, X.; Piao, X.; Bong, D. J. Am. Chem. Soc. 2014, 76, 7265
23. Arambula, J. F.; Ramisetty, S. R.; Baranger, A. M.; Zimmerman, S. C. Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 16068
24. Vysabhattar, R.; Ganesh, K. N. Tetrahedron Lett. 2008, 49, 1314
25. Zhou, Z.; Bong, D. Langmuir 2013, 29, 144-150
26. Ma, M.; Paredes, A.; Bong, D. J. Am. Chem. Soc. 2008, 130, 14456-14458
27. Ma, M.; Gong, Y.; Bong, D. J. Am. Chem. Soc. 2009, 131, 16919-16926
28. Ma, M.; Bong, D. Acc. Chem. Res. 2013, 46, 2988-2997
29. Ma, M.; Bong, D. Org. Biomol. Chem. 2011, 9, 7296-7299
30. Ma, M.; Bong, D. Langmuir 2011, 27, 8841-8853
31. Ma, M.; Bong, D. Langmuir 2011, 27, 1480-1486
32. Felsenfeld, G.; Davies, D. R.; Rich, A. J. Am. Chem. Soc. 1957, 79, 2023
33. Pilch, D. S.; Levenson, C.; Shafer, R. H. Proc. Natl. Acad. Sci. U.S.A. 1990, 87, 1942
34. Betts, L.; Josey, J. A.; Veal, J. M.; Jordan, S. R. Science 1995, 270, 1838
35. Soto, A. M.; Loo, J.; Marky, L. A. J. Am. Chem. Soc. 2002, 124, 14355
36. Duca, M.; Vekhoff, P.; Oussedik, K.; Halby, L.; Arimondo, P. B. Nucleic Acids Res. 2008, 36, 5123
37. Shin, D.; Tor, Y. J. Am. Chem. Soc. 2011, 133, 6926
38. Branda, N.; Kurz, G.; Lehn, J.-M. Chem. Commun. 1996, 2443
39. Chen, H.; Meena; McLaughlin, L. W. J. Am. Chem. Soc. 2008, 130, 13190
40. Largy, E.; Liu, W.; Hasan, A.; Perrin, D. M. ChemBioChem 2013, 14, 2199-2208
41. Mittapalli, G. K.; Reddy, K. R.; Xiong, H.; Munoz, O.; Han, B.; De Riccardis, F.; Krishnamurthy, R.; Eschenmoser, A. Angew. Chem., Int. Ed. 2007, 46, 2470
42. Hysell, M.; Siegel, J. S.; Tor, Y. Org. Biomol. Chem. 2005, 3, 2946
43. Menor-Salván, C.; Ruiz-Bermejo, D.; Guzmán, M. I.; Osuna-Esteban, S.; Veintemillas-Verdaguer, S. Chem.-Eur. J. 2009, 15, 4411
44. Liedl, T.; Olapinski, M.; Simmel, F. C. Angew. Chem., Int. Ed. 2006, 45, 5007
45. Krishnan, Y.; Simmel, F. C. Angew. Chem., Int. Ed. 2011, 50, 3124
46. Chen, X.; Wang, Y.; Liu, Q.; Zhang, Z.; Fan, C.; He, L. Angew. Chem. Int. Ed 2006, 118, 1791
47. Yoshida, W.; Yokobayashi, Y. Chem. Commun. 2007, 195
48. Saghatelian, A.; Völcker, N. H.; Guckian, K. M.; Lin, V. S.-Y.; Ghadiri, M. R. J. Am. Chem. Soc. 2003, 125, 346
49. Chakraborty, S.; Mehtab, S.; Krishnan, Y. Acc. Chem. Res. 2014, 47, 1710
50. Roloff, A.; Seitz, O. Chem. Sci. 2013, 4, 432
51. Dawson, P. E.; Muir, T. W.; Clarklewis, I.; Kent, S. B. H. Science 1994, 266, 776
52. Dose, C.; Ficht, S.; Seitz, O. Angew. Chem., Int. Ed. 2006, 45, 5369
53. Li, X.; Liu, D. R. Angew. Chem., Int. Ed. 2004, 43, 4848
54. Li, Y.; Yongye, A.; Giulianotti, M.; Martinez-Mayorga, K.; Yu, Y.; Houghten, R. A. J. Comb. Chem. 2009, 11, 1066
55. White, C. J.; Yudin, A. K. Nat. Chem. 2011, 3, 509
56. Payne, R. J.; Ficht, S.; Greenberg, W. A.; Wong, C.-H. Angew. Chem., Int. Ed. 2008, 120, 4483
57. Murray, J. B.; Terwey, D. P.; Maloney, L.; Karpeisky, A.; Usman, N.; Beigelman, L.; Scott, W. G. Cell 1998, 92, 665
58. Tuerk, C.; Gold, L. Science 1990, 249, 505
59. Ellington, A. D.; Szostak, J. W. Nature 1990, 346, 818