A simple synthetic replicator amplifies itself from a dynamic reagent pool

Angewandte Chemie - International Edition

Volumn 47, Issue 51, 2008, Pages 9965-9970

  Sadownik, Jan W ^a   Philp, Douglas ^a  

^a UNIVERSITY OF ST ANDREWS   (United Kingdom)

Author keywords

Dynamic covalent chemistry; Molecular recognition; Reaction networks; Self replication; Systems chemistry

Indexed keywords

MOLECULAR RECOGNITION;

DYNAMIC COMBINATORIAL LIBRARIES; DYNAMIC COVALENT CHEMISTRY; EXCHANGE PROCESSES; NONLINEAR KINETICS; REACTION NETWORKS; SELF-REPLICATION; SYSTEMS CHEMISTRY;

MOLECULAR BIOLOGY;

ALDEHYDE; AMIDE; FUSED HETEROCYCLIC RINGS; IMINE; PYRIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; COMBINATORIAL CHEMISTRY; SYNTHESIS;

ALDEHYDES; AMIDES; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; HETEROCYCLIC COMPOUNDS, 2-RING; IMINES; PYRIDINES;

EID: 57549097653     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200804223     Document Type: Article

References (74)

1. a) T. Pawson, Nature 1995, 373, 573-580;
2. b) J. Ricard, Emergent Collective Properties, Networks and Information in Biology, Elsevier, Amsterdam, 2006.
3. a) M. Kindermann, I. Stahl, M. Reimold, W. M. Pankau, G. von Kiedrowski, Angew. Chem. 2005, 117, 6908-6913;
4. Angew. Chem. Int. Ed. 2005, 44, 6750-6755;
5. b) J. Stankiewicz, L. H. Eckardt, Angew. Chem. 2006, 118, 350-352;
6. Angew. Chem. Int. Ed. 2006, 45, 342-344;
7. c) R. F. Ludlow, S. Otto, Chem. Soc. Rev. 2008, 37, 101-108.
8. Z. Dadon, N. Wagner, G. Ashkenasy, Angew. Chem. 2008, 120, 6221-6230;
9. Angew. Chem. Int. Ed. 2008, 47, 6128-6136.
10. a) J.-M. Lehn, Chem. Eur. J. 1999, 5, 2455-2463;
11. b) S. J. Rowan, S. J. Cantrill, G. R. L. Cousins, J. K. M. Sanders, J. F. Stoddart, Angew. Chem. 2002, 114, 938-993;
12. Angew. Chem. Int. Ed. 2002, 41, 898-952;
13. c) K. Severin, Chem. Eur. J. 2004, 10, 2565-2580;
14. d) R. T. S. Lam, A. Belenguer, S. L. Roberts, C. Naumann, T. Jarrosson, S. Otto, J. K. M. Sanders, Science 2005, 308, 667-669;
15. e) P. T. Corbett, J. Leclaire, L. Vial, K. R. West, J. L. Wietor, J. K. M. Sanders, S. Otto, Chem. Rev. 2006, 106, 3652-3711;
16. f) J. R. Nitschke, Acc. Chem. Res. 2007, 40, 103-112;
17. g) S. Ladame, Org. Biomol. Chem. 2008, 6, 219-226.
18. a) J. D. Cheeseman, A. D. Corbett, J. L. Gleason, R. J. Kazlauskas, Chem. Eur. J. 2005, 11, 1708-1716;
19. b) A. V. Eliseev, M. I. Nelen, J. Am. Chem. Soc. 1997, 119, 1147-1148;
20. c) Y. Kubota, S. Sakamoto, K. Yamaguchi, M. Fujita, Proc. Natl. Acad. Sci. USA 2002, 99, 4854-4856.
21. a) S. Otto, S. Kubik, J. Am. Chem. Soc. 2003, 125, 7804-7805;
22. b) A. Gonzalez-Alvarez, I. Alfonso, F. Lopez-Ortiz, A. Aguirre, S. Garcia-Granada, V. Gotor, Eur. J. Org. Chem. 2004, 1117-1127;
23. c) A. Buryak, K. Severin, Angew. Chem. 2005, 117, 8149-8152;
24. Angew. Chem. Int. Ed. 2005, 44, 7935-7938;
25. d) P. T. Corbett, J. K. M. Sanders, S. Otto, J. Am. Chem. Soc. 2005, 127, 9390-9392;
26. e) S. Otto, K. Severin, Top. Curr. Chem. 2007, 277, 267-288;
27. f) F. Bulos, S. L. Roberts, R. L. E. Furlan, J. K. M. Sanders, Chem. Commun. 2007, 3092-3093.
28. a) E. Stulz, S. M. Scott, A. D. Bond, S. J. Teat, J. K. M. Sanders, Chem. Eur. J. 2003, 9, 6039-6048;
29. b) K. S. Chichak, S. J. Cantrill, A. R. Pease, S.-H. Chiu, G. W. V. Cave, J. L. Atwood, J. F. Stoddart, Science 2004, 304, 1308-1312;
30. c) J.-M. Lehn, Chem. Soc. Rev. 2007, 36, 151-160;
31. d) C. D. Meyer, C. S. Joiner, J. F. Stoddart, Chem. Soc. Rev. 2007, 36, 1705-1723;
32. e) R. F. Ludlow, J. Liu, H. Li, S. L. Roberts, J. K. M. Sanders, S. Otto, Angew. Chem. 2007, 119, 5864-5866;
33. Angew. Chem. Int. Ed. 2007, 46, 5762-5764;
34. f) P. C. Haussmann, S. I. Khan, J. F. Stoddart, J. Org. Chem. 2007, 72, 6708-6713;
35. g) D. Schultz, J. R. Nitschke, Chem. Eur. J. 2007, 13, 3660-3665.
36. a) I. Huc, J.-M. Lehn, Proc. Natl. Acad. Sci. USA 1997, 94, 2106-2110;
37. b) J. D. Cheeseman, A. D. Corbett, R. Shu, J. Croteau, J. L. Gleason, R. J. Kazlauskas, J. Am. Chem. Soc. 2002, 124, 5692-5701;
38. c) M. Hochgürtel, R. Biesinger, H. Kroth, D. Piecha, M. W. Hofmann, S. Krause, O. Schaaf, C. Nicolau, A. V. Eliseev, J. Med. Chem. 2003, 46, 356-358;
39. d) O. Ramström, S. Lohmann, T. Bunyapaiboonsri, J.-M. Lehn, Chem. Eur. J. 2004, 10, 1711-1715;
40. e) L. Milanesi, C. A. Hunter, S. E. Sedelinkova, J. P. Waltho, Chem. Eur. J. 2006, 12, 1081-1087;
41. f) B. Shi, R. Stevenson, D. J. Campopiano, M. F. Greaney, J. Am. Chem. Soc. 2006, 128, 8459-8467.
42. a) K. Severin, Chem. Eur. J. 2004, 10, 2565-2580;
43. b) P. T. Corbett, S. Otto, J. K. M. Sanders, Chem. Eur. J. 2004, 10, 3139-3143;
44. c) B. de Bruin, P. Hauwert, J. N. H. Reek, Angew. Chem. 2006, 118, 2726-2729;
45. Angew. Chem. Int. Ed. 2006, 45, 2660-2663;
46. d) P. T. Corbett, J. K. M. Sanders, S. Otto, Angew. Chem. 2007, 119, 9014-9017;
47. Angew. Chem. Int. Ed. 2007, 46, 8858-8861.
48. E. M. Galimov, Origins Life Evol. Biosphere 2004, 34, 599-613.
49. A. Kornberg, J. Biol. Chem. 1988, 263, 1-4.
50. J. B. A. Green, Nat. Cell Biol. 2008, 10, 375-377.
51. P. R. Wills, Biosystems 2001, 60, 49-57.
52. M. Freeman, Nature 2000, 408, 313-319.
53. A. Eschenmoser, Tetrahedron 2007, 63, 12821-12844.
54. R. Shapiro, Q. Rev. Biol. 2006, 81, 105-125.
55. G. Ashkenasy, R. Jagasia, M. Yadav, M. R. Ghadiri, Proc. Natl. Acad. Sci. USA 2004, 101, 10872-10877.
56. a) E. A. Wintner, J. Rebek, Jr., Acta. Chem. Scand. 1996, 50, 469-485;
57. b) D. H. Lee. K. Severin, M. R. Ghadiri, Curr. Opin. Chem. Biol. 1997, 1, 491-496;
58. c) A. Robertson, A. J. Sinclair, D. Philp, Chem. Soc. Rev. 2000, 29, 141-152;
59. d) V. Patzke, G. von Kiedrowski, ARKIVOC 2007, 5, 293-310;
60. e) A. Vidonne, D. Philp, Eur. J. Org. Chem. 2008, DOI: 10.1002/ejoc.200800827.
61. A. Pross, Origins Life Evol. Biosphere 2004, 34, 307-321.
62. a) T. Shibata, S. Yonekubo, K. Soai, Angew. Chem. 1999, 111, 746-748;
63. Angew. Chem. Int. Ed. 1999, 38, 659-661;
64. b) D. G. Blackmond, Adv. Synth. Catal. 2002, 344, 156-158.
65. a) S. Xu, N. Giuseppone, J. Am. Chem. Soc. 2008, 130, 1826-1827;
66. b) V. del Amo, A. M. Z. Slawin, D. Philp, Org. Lett. 2008, 10, 4589-4592.
67. E. Kassianidis, D. Philp, Angew. Chem. 2006, 118, 6492-6496;
68. Angew. Chem. Int. Ed. 2006, 45, 6344-6348.
69. S. M. Turega, C. Lorenz, J. W. Sadownik, D. Philp, Chem. Commun. 2008, 4076-4078.
70. The descriptors cis and trans identify the relative configuration of the three protons located on the bicyclic fused ring structure formed in the cycloaddition reaction. In the cis cycloadduct all three protons lie on the same face of the fused ring system. In the trans cycloadduct, the two protons originally located on the maleimide are located on the opposite face to the proton originating from the nitrone.
71. The addition of the replicator at the start of the experiment should remove the lag or induction period associated with the necessary formation of replicator through the slow, bimolecular pathway. Therefore, seeding the reaction with replicator should permit the formation of the replicator at the maximum autocatalytic rate from t = 0. In this case, at t = 0, the concentration of nitrone 3 is zero and the induction period apparent in the formation of trans-7b arises from the necessary formation of nitrone 3 by exchange.
72. -1 at 5 h) observed in the reaction between 3 and 5b in the absence of dynamic exchange. This result suggests that in the presence of added template the replication of trans-7b is the dominant irreversible reaction pathway in the system from the start of the experiment. See Supporting Information (Figure S8) for rate vs. time profiles.
73. Replicator trans-7b has a molecular weight of only 580 Da, possesses only three stereocentres and the system relies on a single recognition motif for its function. Therefore, in comparison to nucleic acids, it can be considered to be structurally and informationally simple.
74. E. Kassianidis, D. Philp, Chem. Commun. 2006, 4072-4074.