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Self-Replication A Brief Introduction To Self-propagating Chemical Information TSRI Chemistry Journal Club 5/11/07 Brian Frezza
Why Study Chemical Self-Replication ,[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object]
A Broader Definition of Self-Replication  ,[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],T •T A + B T B A B
Talk Outline ,[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],*unpublished work
Ligation Based Self-Replication ɛ = k*/k Bg k Bg
Ligation Based Self-Replication ,[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object]
Hexadeoxynucleotide Self-Replication Kiedrowski, G.  Angew. Chem. Int. Ed.   1986 ,  25 , 932-935.
Hexadeoxynucleotide Self-Replication Kiedrowski, G.  Angew. Chem. Int. Ed.   1986 ,  25 , 932-935.
Hexadeoxynucleotide Self-Replication P = 0.48 ɛ = ~25 Kiedrowski, G.  Angew. Chem. Int. Ed.   1986 ,  25 , 932-935. 0 mM Template 0.2 mM Template 0.4 mM Template 0.8 mM Template
RNA Ligase Self-Replication  Paul, N.; Joyce, G. F.  Proc. Natl. Acad. Sci. U. S. A.   2002 ,  99 , 12733-40.
RNA Ligase Self-Replication  Paul, N.; Joyce, G. F.  Proc. Natl. Acad. Sci. U. S. A.   2002 ,  99 , 12733-40.
RNA Ligase Self-Replication  P = ~1 ɛ = 3.0*10 8 Paul, N.; Joyce, G. F.  Proc. Natl. Acad. Sci. U. S. A.   2002 ,  99 , 12733-40.
Peptide Self-Replication Lee, D. H.; Granja, J. R.; Martinez, J. A.; Severin, K.; Ghadri, M. R.  Nature   1996 ,  382 , 525-8.
Peptide Self-Replication Lee, D. H.; Granja, J. R.; Martinez, J. A.; Severin, K.; Ghadri, M. R.  Nature   1996 ,  382 , 525-8.
Peptide Self-Replication Lee, D. H.; Granja, J. R.; Martinez, J. A.; Severin, K.; Ghadri, M. R.  Nature   1996 ,  382 , 525-8. 0 uM Template 5 uM Template 10 uM Template 20 uM Template 40 uM Template P = ~0.5 ɛ = ~500
Peptide Self-Replication ,[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object]
Small Molecule Self-Replication Tjivikua, T.; Ballester, P.; Rebek, J.  J. Am. Chem. Soc.   1990 ,  112 , 1249-1250. Wintner, E. A.; Conn, M. M.; Rebek, J.  J. Am. Chem. Soc.  1994 ,  116 , 8877-8884.
Small Molecule Self-Replication Tjivikua, T.; Ballester, P.; Rebek, J.  J. Am. Chem. Soc.   1990 ,  112 , 1249-1250. A + B T A • B • T T • T Wintner, E. A.; Conn, M. M.; Rebek, J.  J. Am. Chem. Soc.  1994 ,  116 , 8877-8884. +
Small Molecule Self-Replication Tjivikua, T.; Ballester, P.; Rebek, J.  J. Am. Chem. Soc.   1990 ,  112 , 1249-1250. Wintner, E. A.; Conn, M. M.; Rebek, J.  J. Am. Chem. Soc.  1994 ,  116 , 8877-8884. P = ~0.5 ɛ = ~22 A + B T
Small Molecule Self-Replication Terfort, A.; Kiedrowski, G.  Angew. Chem. Int. Ed.  1992 ,  31 , 654-656.
Small Molecule Self-Replication Terfort, A.; Kiedrowski, G.  Angew. Chem. Int. Ed.  1992 ,  31 , 654-656.
Small Molecule Self-Replication Terfort, A.; Kiedrowski, G.  Angew. Chem. Int. Ed.  1992 ,  31 , 654-656. P = ~0.5 ɛ = ~16.4 0 Equiv. Template 0.1 Equiv. Template 0.2 Equiv. Template 0.4 Equiv. Template
Small Molecule Self-Replication Pearson, R. J.; Kassianidis, E.; Slawin, A. M.; Philp, D.   Org. Biomol. Chem.  2004 ,  2 , 3434-41. Kassianidis, E.; Philp, D.  Chem. Commun.  2006 , 4072-4. Kassianidis, E.; Philp, D.  Angew. Chem. Int. Ed.  2006 ,  45 , 6344-6348. Pearson, R. J.; Kassianidis, E.; Slawin, A. M.; Philp, D.  Chen. Eur. J.  2006 ,  12 , 6829-40.
Small Molecule Self-Replication Pearson, R. J.; Kassianidis, E.; Slawin, A. M.; Philp, D.   Org. Biomol. Chem.  2004 ,  2 , 3434-41. A + B T Kassianidis, E.; Philp, D.  Chem. Commun.  2006 , 4072-4. Kassianidis, E.; Philp, D.  Angew. Chem. Int. Ed.  2006 ,  45 , 6344-6348. Pearson, R. J.; Kassianidis, E.; Slawin, A. M.; Philp, D.  Chen. Eur. J.  2006 ,  12 , 6829-40. +
Small Molecule Self-Replication Pearson, R. J.; Kassianidis, E.; Slawin, A. M.; Philp, D.   Org. Biomol. Chem.  2004 ,  2 , 3434-41. Kassianidis, E.; Philp, D.  Chem. Commun.  2006 , 4072-4. Kassianidis, E.; Philp, D.  Angew. Chem. Int. Ed.  2006 ,  45 , 6344-6348. Pearson, R. J.; Kassianidis, E.; Slawin, A. M.; Philp, D.  Chen. Eur. J.  2006 ,  12 , 6829-40. P = ~0.1 ɛ = ~8
Cleavage Based Self-Replication ,[object Object],[object Object],A + A A•A A
Cross-Catalytic Ribozymes Levy, M.; Ellington, A. D.  Proc. Natl. Acad. Sci. U. S. A.  2003 ,  100 , 6416-6421.
Cross-Catalytic Ribozymes Levy, M.; Ellington, A. D.  Proc. Natl. Acad. Sci. U. S. A.  2003 ,  100 , 6416-6421. P = 1 ɛ = 1.2*10 9
Autopoiesis ,[object Object]
Reverse Micelles Bachmann, P. A.; Walde, P.; Luisi, P. L.; Lang, J.  J. Am. Chem. Soc.  1990 ,  112 , 8200-8201. Bachmann, P. A.; Walde, P.; Luisi, P. L.; Lang, J.  J. Am. Chem. Soc.  1991 ,  113 , 8204-8209. Bachmann, P. A.; Luisi, P. L.; Lang, J.  Nature  1992 ,  357 , 57-59.
Reverse Micelles Bachmann, P. A.; Walde, P.; Luisi, P. L.; Lang, J.  J. Am. Chem. Soc.  1990 ,  112 , 8200-8201. Bachmann, P. A.; Walde, P.; Luisi, P. L.; Lang, J.  J. Am. Chem. Soc.  1991 ,  113 , 8204-8209. Bachmann, P. A.; Luisi, P. L.; Lang, J.  Nature  1992 ,  357 , 57-59.
Reverse Micelles Bachmann, P. A.; Walde, P.; Luisi, P. L.; Lang, J.  J. Am. Chem. Soc.  1990 ,  112 , 8200-8201. Bachmann, P. A.; Walde, P.; Luisi, P. L.; Lang, J.  J. Am. Chem. Soc.  1991 ,  113 , 8204-8209. Bachmann, P. A.; Luisi, P. L.; Lang, J.  Nature  1992 ,  357 , 57-59.
Locational Self-Replication ,[object Object],X X X X X X X X X X X X  + X
Encapsulated Reagents Chen, J.; Korner, S.; Craig, S. L.; Lin, S.; Rudkevich, D. M.; Rebek, J., Jr.  Proc. Natl. Acad. Sci. U. S. A.  2002 ,  99 , 2593-6.
Encapsulated Reagents Chen, J.; Korner, S.; Craig, S. L.; Lin, S.; Rudkevich, D. M.; Rebek, J., Jr.  Proc. Natl. Acad. Sci. U. S. A.  2002 ,  99 , 2593-6.
Conformation Based Self-Replication ,[object Object],A* • A* A A*
Hybridization Chain Reaction (HCR) + Dirks, R. M.; Pierce, N. A.  Proc. Natl. Acad. Sci. U. S. A.  2004 ,  101 , 15275-8. B’ A’ B’ B A’ C’ + B’ B C A
Prions and Amyloids ,[object Object],A* A (A* •  A*•) n
Conclusions ,[object Object],[object Object],[object Object],[object Object],[object Object]

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Self-replicating Molecules: An introduction

  • 1. Self-Replication A Brief Introduction To Self-propagating Chemical Information TSRI Chemistry Journal Club 5/11/07 Brian Frezza
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  • 7. Hexadeoxynucleotide Self-Replication Kiedrowski, G. Angew. Chem. Int. Ed. 1986 , 25 , 932-935.
  • 8. Hexadeoxynucleotide Self-Replication Kiedrowski, G. Angew. Chem. Int. Ed. 1986 , 25 , 932-935.
  • 9. Hexadeoxynucleotide Self-Replication P = 0.48 ɛ = ~25 Kiedrowski, G. Angew. Chem. Int. Ed. 1986 , 25 , 932-935. 0 mM Template 0.2 mM Template 0.4 mM Template 0.8 mM Template
  • 10. RNA Ligase Self-Replication Paul, N.; Joyce, G. F. Proc. Natl. Acad. Sci. U. S. A. 2002 , 99 , 12733-40.
  • 11. RNA Ligase Self-Replication Paul, N.; Joyce, G. F. Proc. Natl. Acad. Sci. U. S. A. 2002 , 99 , 12733-40.
  • 12. RNA Ligase Self-Replication P = ~1 ɛ = 3.0*10 8 Paul, N.; Joyce, G. F. Proc. Natl. Acad. Sci. U. S. A. 2002 , 99 , 12733-40.
  • 13. Peptide Self-Replication Lee, D. H.; Granja, J. R.; Martinez, J. A.; Severin, K.; Ghadri, M. R. Nature 1996 , 382 , 525-8.
  • 14. Peptide Self-Replication Lee, D. H.; Granja, J. R.; Martinez, J. A.; Severin, K.; Ghadri, M. R. Nature 1996 , 382 , 525-8.
  • 15. Peptide Self-Replication Lee, D. H.; Granja, J. R.; Martinez, J. A.; Severin, K.; Ghadri, M. R. Nature 1996 , 382 , 525-8. 0 uM Template 5 uM Template 10 uM Template 20 uM Template 40 uM Template P = ~0.5 ɛ = ~500
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  • 17. Small Molecule Self-Replication Tjivikua, T.; Ballester, P.; Rebek, J. J. Am. Chem. Soc. 1990 , 112 , 1249-1250. Wintner, E. A.; Conn, M. M.; Rebek, J. J. Am. Chem. Soc. 1994 , 116 , 8877-8884.
  • 18. Small Molecule Self-Replication Tjivikua, T.; Ballester, P.; Rebek, J. J. Am. Chem. Soc. 1990 , 112 , 1249-1250. A + B T A • B • T T • T Wintner, E. A.; Conn, M. M.; Rebek, J. J. Am. Chem. Soc. 1994 , 116 , 8877-8884. +
  • 19. Small Molecule Self-Replication Tjivikua, T.; Ballester, P.; Rebek, J. J. Am. Chem. Soc. 1990 , 112 , 1249-1250. Wintner, E. A.; Conn, M. M.; Rebek, J. J. Am. Chem. Soc. 1994 , 116 , 8877-8884. P = ~0.5 ɛ = ~22 A + B T
  • 20. Small Molecule Self-Replication Terfort, A.; Kiedrowski, G. Angew. Chem. Int. Ed. 1992 , 31 , 654-656.
  • 21. Small Molecule Self-Replication Terfort, A.; Kiedrowski, G. Angew. Chem. Int. Ed. 1992 , 31 , 654-656.
  • 22. Small Molecule Self-Replication Terfort, A.; Kiedrowski, G. Angew. Chem. Int. Ed. 1992 , 31 , 654-656. P = ~0.5 ɛ = ~16.4 0 Equiv. Template 0.1 Equiv. Template 0.2 Equiv. Template 0.4 Equiv. Template
  • 23. Small Molecule Self-Replication Pearson, R. J.; Kassianidis, E.; Slawin, A. M.; Philp, D. Org. Biomol. Chem. 2004 , 2 , 3434-41. Kassianidis, E.; Philp, D. Chem. Commun. 2006 , 4072-4. Kassianidis, E.; Philp, D. Angew. Chem. Int. Ed. 2006 , 45 , 6344-6348. Pearson, R. J.; Kassianidis, E.; Slawin, A. M.; Philp, D. Chen. Eur. J. 2006 , 12 , 6829-40.
  • 24. Small Molecule Self-Replication Pearson, R. J.; Kassianidis, E.; Slawin, A. M.; Philp, D. Org. Biomol. Chem. 2004 , 2 , 3434-41. A + B T Kassianidis, E.; Philp, D. Chem. Commun. 2006 , 4072-4. Kassianidis, E.; Philp, D. Angew. Chem. Int. Ed. 2006 , 45 , 6344-6348. Pearson, R. J.; Kassianidis, E.; Slawin, A. M.; Philp, D. Chen. Eur. J. 2006 , 12 , 6829-40. +
  • 25. Small Molecule Self-Replication Pearson, R. J.; Kassianidis, E.; Slawin, A. M.; Philp, D. Org. Biomol. Chem. 2004 , 2 , 3434-41. Kassianidis, E.; Philp, D. Chem. Commun. 2006 , 4072-4. Kassianidis, E.; Philp, D. Angew. Chem. Int. Ed. 2006 , 45 , 6344-6348. Pearson, R. J.; Kassianidis, E.; Slawin, A. M.; Philp, D. Chen. Eur. J. 2006 , 12 , 6829-40. P = ~0.1 ɛ = ~8
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  • 27. Cross-Catalytic Ribozymes Levy, M.; Ellington, A. D. Proc. Natl. Acad. Sci. U. S. A. 2003 , 100 , 6416-6421.
  • 28. Cross-Catalytic Ribozymes Levy, M.; Ellington, A. D. Proc. Natl. Acad. Sci. U. S. A. 2003 , 100 , 6416-6421. P = 1 ɛ = 1.2*10 9
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  • 30. Reverse Micelles Bachmann, P. A.; Walde, P.; Luisi, P. L.; Lang, J. J. Am. Chem. Soc. 1990 , 112 , 8200-8201. Bachmann, P. A.; Walde, P.; Luisi, P. L.; Lang, J. J. Am. Chem. Soc. 1991 , 113 , 8204-8209. Bachmann, P. A.; Luisi, P. L.; Lang, J. Nature 1992 , 357 , 57-59.
  • 31. Reverse Micelles Bachmann, P. A.; Walde, P.; Luisi, P. L.; Lang, J. J. Am. Chem. Soc. 1990 , 112 , 8200-8201. Bachmann, P. A.; Walde, P.; Luisi, P. L.; Lang, J. J. Am. Chem. Soc. 1991 , 113 , 8204-8209. Bachmann, P. A.; Luisi, P. L.; Lang, J. Nature 1992 , 357 , 57-59.
  • 32. Reverse Micelles Bachmann, P. A.; Walde, P.; Luisi, P. L.; Lang, J. J. Am. Chem. Soc. 1990 , 112 , 8200-8201. Bachmann, P. A.; Walde, P.; Luisi, P. L.; Lang, J. J. Am. Chem. Soc. 1991 , 113 , 8204-8209. Bachmann, P. A.; Luisi, P. L.; Lang, J. Nature 1992 , 357 , 57-59.
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  • 34. Encapsulated Reagents Chen, J.; Korner, S.; Craig, S. L.; Lin, S.; Rudkevich, D. M.; Rebek, J., Jr. Proc. Natl. Acad. Sci. U. S. A. 2002 , 99 , 2593-6.
  • 35. Encapsulated Reagents Chen, J.; Korner, S.; Craig, S. L.; Lin, S.; Rudkevich, D. M.; Rebek, J., Jr. Proc. Natl. Acad. Sci. U. S. A. 2002 , 99 , 2593-6.
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  • 37. Hybridization Chain Reaction (HCR) + Dirks, R. M.; Pierce, N. A. Proc. Natl. Acad. Sci. U. S. A. 2004 , 101 , 15275-8. B’ A’ B’ B A’ C’ + B’ B C A
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