Self-duplicating amplification in a dynamic combinatorial library

Journal of the American Chemical Society

Volumn 130, Issue 6, 2008, Pages 1826-1827

  Xu, Shengguang ^a   Giuseppone, Nicolas ^b  

^a SHANDONG UNIVERSITY   (China)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE; ALDEHYDE; AMINE; CHLOROFORM; DEUTERIUM;

ARTICLE; COMBINATORIAL LIBRARY; DIMERIZATION; HYDROGEN BOND; MASS SPECTROMETRY; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOSPECIFICITY; THERMODYNAMICS;

EID: 39049158889     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja710248q     Document Type: Article

References (29)

1. Lehn, J.-M. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4763-4768.
2. For reviews on dynamic combinatorial chemistry, see for instance: (a) Lehn, J.-M. Chem. Eur. J. 1999, 5, 2455-2463.
3. (b) Rowan, S. J.; Cantrill, S. J.; Cousins, G. R. L.; Sanders, J. K. M.; Stoddart, J. F. Angew. Chem., Int. Ed. 2002, 41, 898-952.
4. (c) Corbett, P. T.; Leclaire, J.; Vial, J.; West, K. R.; Wietor, J.-L.; Sanders, J. K. M.; Otto, S. Chem. Rev. 2006, 106, 3652-3711.
5. (a) Ramström, O.; Lehn, J.-M. Nature Rev. Drug Discovery 2001, 1, 26-36.
6. (b) Cheeseman, J. D.; Corbett, A. D.; Gleason, J. L.; Kazlauskas, R. J. Chem. Eur. J. 2005, 11, 1708-1716.
7. For examples of recent advances, see for instance: (a) Severin, K. Chem. Eur. J. 2004, 10, 2565-2580.
8. (b) Saur, I.; Scopelliti, R.; Severin, K. Chem. Eur. J. 2006, 12, 1058-1066.
9. (c) Giuseppone, N.; Schmitt, J.-L.; Lehn, J.-M. J. Am. Chem. Soc. 2006, 128, 16748-16763.
10. (d) Nitschke, J. R. Acc. Chem. Res. 2007, 40, 103-112.
11. (e) Vongvilai, P.; Angelin, M.; Larsson, R.; Ramström, O. Angew. Chem., Int. Ed. 2007, 46, 948-950.
12. (f) Kerckhoffs, J. M. C. A.; Mateos-Timoneda, M. A.; Reinhoudt, D. N.; Crego-Calama, M. Chem. Eur. J. 2007, 2377-2485.
13. (g) Ludlow, R. F.; Liu, J.; Li, H.; Roberts, S. L.; Sanders, J. K. M.; Otto, S. Angew. Chem., Int. Ed. 2007, 46, 5762-5764.
14. (h) Legrand, Y.-M.; van der Lee, A.; Barboiu, M. Inorg. Chem. 2007, 46, 9540-9547.
15. (a) Giuseppone, N.; Lehn, J.-M. Chem.-Eur. J. 2006, 12, 1715-1722.
16. (b) Giuseppone, N.; Fuks, G.; Lehn, J.-M. Chem. Eur. J. 2006, 12, 1723-1735.
17. (c) Giuseppone, N.; Lehn, J.-M. Angew. Chem., Int. Ed. 2006, 45, 4619-4624.
18. Lehn, J.-M. Chem. Soc. Rev. 2007, 36, 151-160.
19. For reviews on self-replication, see: (a) Morgan Conn, M.; Rebek, J. Curr. Opin. Struct. Biol. 1994, 4, 629-635.
20. (b) Robertson, A.; Sinclair, A. J.; Philp, D. Chem. Soc. Rev. 2000, 29, 141-152.
21. (c) Paul, N.; Joyce, G. F. Curr. Opin. Chem. Biol. 2004, 8, 634-639.
22. (d) Patzke, V.; von Kiedrowski, G. ARKIVOC 2007, 293-310.
23. For a study of the kinetic acceleration of a single imine condensation upon the initial addition of the final product, see: (e) Terfort, A.; von Kiedrowski, G. Angew. Chem., Int. Ed. 1992, 31, 654-656.
24. (a) Tjivikua, T.; Baluster, R.; Rebek, J. J. Am. Chem. Soc. 1990, 112, 1249-1250.
25. (b) Nowick, J. S.; Feng, Q.; Tjivikua, T.; Ballester, P.; Rebek, J. J. Am. Chem. Soc. 1991, 113, 8831-8839.
26. The corresponding Rebek "self-replicator" is made by the association of adenosine amine 1 and a Kemp's imide activated ester, producing an irreversible amide bond instead of a reversible imine bond in our case.
27. Askew, B.; Ballester, P.; Buhr, C.; Jeong, K. S.; Jones, S.; Parris, K.; Williams, K.; Rebek, J. J. Am. Chem. Soc. 1989, 111, 1082-1090.
28. Constituents directly related through one of their components may be considered as antagonists (increasing one, decreases the others), whereas constituents with no common component behave as agonists (increasing one, increases the other), as defined in reference 5a; see also 4a.
29. We use the term "self-replication" for auto-catalytic systems displaying a sigmoid concentration-time profile and the term "self-duplication" for a system displaying the general property to thermodynamically or kinetically (or both) favor its own formation (see also SI).