Simultaneous and orthogonal covalent exchange processes in dynamic combinatorial libraries

Journal of Combinatorial Chemistry

Volumn 12, Issue 4, 2010, Pages 410-413

  Escalante, Andrea M ^a   Orrillo, A Gastón ^a   Furlan, Ricardo L E ^a  

^a Facultad de Ciencias Naturales e Instituto M Lillo   (Argentina)

Author keywords

[No Author keywords available]

Indexed keywords

DISULFIDE; HYDRAZONE DERIVATIVE; THIOL DERIVATIVE; MOLECULAR LIBRARY;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; COMPUTER SIMULATION; MOLECULAR LIBRARY;

COMBINATORIAL CHEMISTRY TECHNIQUES; COMPUTER SIMULATION; DISULFIDES; HYDRAZONES; MOLECULAR STRUCTURE; SMALL MOLECULE LIBRARIES; SULFHYDRYL COMPOUNDS;

EID: 77954546907     PISSN: 15204766     EISSN: 15204774     Source Type: Journal    
DOI: 10.1021/cc100046r     Document Type: Article

References (34)

1. Corbett, P. T., Leclaire, J., Vial, L., West, K. R., Wietor, J.-L., Sanders, J. K. M., and Otto, S. Chem. Rev. 2006, 106, 3652-3711
2. Lehn, J.-M. Chem. Soc. Rev. 2007, 36, 151-160
3. Otto, S., Furlan, R. L. E., and Sanders, J. K. M. Curr. Opin. Chem. Biol. 2002, 6, 321-327
4. Cousins, G. R. L., Poulsen, S. A., and Sanders, J. K. M. Chem. Commun. 1999, 1575-1576
5. Nguyen, R. and Huc, I. Chem. Commun. 2003, 942-943
6. Lees, G. W. J. and Whitesides, M. J. Org. Chem. 1993, 58, 642-647
7. Ramström, O. and Lehn, J.-M. ChemBioChem. 2000, 1, 41-47
8. Otto, S., Furlan, R. L. E., and Sanders, J. K. M. J. Am. Chem. Soc. 2000, 122, 12063-12064
9. Otto, S., Furlan, R. L. E., and Sanders, J. K. M. Science 2002, 297, 590-593
10. Larsson, R., Pei, Z., and Ramstrom, O. Angew. Chem., Int. Ed. 2004, 43, 3716-3718
11. Woll, M. G. and Gellman, S. H. J. Am. Chem. Soc. 2004, 126, 11172-11174
12. Leclaire, J., Vial, L., Otto, S., and Sanders, J. K. M. Chem. Commun. 2005, 1959-1961
13. Sarma, R. J., Otto, S., and Nitschke, J. R. Chem. - Eur. J. 2007, 13, 9542-9546
14. Goral, V., Nelen, M. I., Eliseev, A. V., and Lehn, J.-M. Proc. Natl. Acad. Sci. 2001, 98, 1347-1352
15. Rodriguez-Docampo, Z. and Otto, S. Chem. Commun. 2008, 5301-5303
16. Orrillo, A. G., Escalante, A. M., and Furlan, R. L. E. Chem. Commun. 2008, 5298-5300
17. Moore, J. S. and Zimmerman, N. W. Org. Lett. 2000, 2, 915-918
18. Corbett, P. T., Otto, S., and Sanders, J. K. M. Org. Lett. 2004, 6, 1825-1827
19. Furlan, R. L. E., Ng, Y.-F., Cousins, G. R. L., Redman, J. E., and Sanders, J. K. M. Tetrahedron 2002, 58, 771-778
20. Hioki, H. and Still, W. C. J. Org. Chem. 1998, 63, 904-905
21. ten Cate, A. T., Dankers, P. W. D., Sijbesma, R. P., and Meijer, E. W. J. Org. Chem. 2005, 70, 5799-5803
22. Zervas, L., Benoiton, L., Weiss, E., Winitz, M., and Greentein, J. P. J. Am. Chem. Soc. 1959, 81, 1729-1734
23. Rajaram, S., Reddy, G. S., and Iyengar, D. S. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1999, 38, 639-640
24. Kieran, A. L., Bond, A. D., Belenger, A. M., and Sanders, J. K. M. Chem.Commun. 2003, 2674-2675
25. In all the experiments the equilibrium was assumed through the confirmation that the library composition stayed constant during 24 h.
26. 2 atmosphere, some oxygen was initially present in the system leading to partial oxidation of thiols.
27. Apparent partial decomposition of thioester 4 was observed at 24 h of reaction in the experiments with TEA. No precipitation was observed in this experiment.
28. Two equivalents of thiophenol (5) were added for each equivalent of disulfide 6, and another two equivalents were added for each equivalent of thioester 4. This relative amount was used to ensure the presence of nucleophile during the entire process despite the partial oxidation of thiophenol in previous experiments.
29. Since natural evolution is a process operating far from the equilibrium state, most of chemical evolutionary research has been conducted in kinetics-driven systems. Examples of chemical "irreversible" evolution
30. Robertson, A., Sinclair, A. J., and Philp, D. Chem. Soc. Rev. 2000, 29, 141-152
31. Patzke, V. and von Kiedrowski, G. ARKIVOC 2007, 338, 293-310. The implementation of adaptation-selection cycles in DCLs would allow unveiling the evolution of chemical entities in an unexplored direction
32. In an analogy with the diversity oriented synthesis (DOS) strategy. In this sense, a compromise between target and diversity oriented synthesis is needed to be considered in DCLs. For a review about DOS, see: Burke, M. D. and Schreiber, S. L. Angew. Chem., Int. Ed. 2004, 43, 46-58
33. Zaubitzer, F., Riis-Johannessen, T., and Severin, K. Org. Biomol. Chem. 2009, 7, 4598-4603
34. Buryak, A., Zaubitzer, F., Pozdnoukhov, A., and Severin, K. J. Am. Chem. Soc. 2008, 130, 11260-11261