A supramolecular approach to an allosteric catalyst

Journal of the American Chemical Society

Volumn 125, Issue 35, 2003, Pages 10508-10509

  Gianneschi, Nathan C ^a   Bertin, Paul A ^a   Nguyen, SonBinh T ^a   Mirkin, Chad A ^a   Zakharov, Lev N ^b   Rheingold, Arnold L ^b  

^a NORTHWESTERN UNIVERSITY   (United States)

^b UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANE OXIDE;

ARTICLE; CATALYST; CHEMICAL REACTION; COMPLEX FORMATION; ENZYME ACTIVE SITE; REACTION ANALYSIS; RING OPENING; STEREOCHEMISTRY; SUPRAMOLECULAR CHEMISTRY;

EID: 0042355723     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja035621h     Document Type: Article

References (25)

1. Allosteric regulation of catalysts is the control of activity by the reversible binding of small molecules to structural sites that are remote from, but induce, conformational changes at the active site. (a) Fritsky, I. O.; Ott, R.; Kramer, R. Angew. Chem., Int. Ed. 2000, 39, 3255-3258. (b) Fritsky, I. O.; Ott, R.; Pritzkow, H.; Kramer, R. Chem.-Eur. J. 2001, 7, 1221-1231.
2. Allosteric regulation of catalysts is the control of activity by the reversible binding of small molecules to structural sites that are remote from, but induce, conformational changes at the active site. (a) Fritsky, I. O.; Ott, R.; Kramer, R. Angew. Chem., Int. Ed. 2000, 39, 3255-3258. (b) Fritsky, I. O.; Ott, R.; Pritzkow, H.; Kramer, R. Chem.-Eur. J. 2001, 7, 1221-1231.
3. (a) Caulder, D. L.; Raymond, K. N. Acc. Chem. Res. 1999, 32, 975-982.
4. (b) Leininger, S.; Olenyuk, B.; Stang, P. J. Chem. Rev. 2000, 100, 853-907.
5. (c) Swiegers, G. F.; Malefetse, T. J. Chem. Rev. 2000, 100, 3483-3538.
6. (d) Holliday, B. J.; Mirkin, C. A. Angew. Chem., Int. Ed. 2001, 40, 2022-2043.
7. (e) Cotton, F. A.; Lin, C.; Murillo, C. A. Acc. Chem. Res. 2001, 34, 759-771.
8. (f) Fujita, M.; Umemoto, K.; Yoshizawa, M.; Fujita, N.; Kusukawa, T.; Biradha, K. Chem. Commun. 2001, 509-518.
9. (a) Merlau, M. L.; del Pilar Mejia, M.; Nguyen, S. T.; Hupp, J. T. Angew. Chem., Int. Ed. 2001, 113, 4369-4372.
10. (b) Lee, S.-J.; Hu, A.; Lin, W. J. Am. Chem. Soc. 2002, 124, 12948-12949.
11. (c) Nakash, M.; Clyde-Watson, Z.; Feeder, N.; Davies, J. E.; Teat, S. J. ; Sanders, J. K. M. J. Am. Chem. Soc. 2000, 122, 5286-5293.
12. (a) Farrell, J. R.; Mirkin, C. A.; Liable-Sands, L. M.; Rheingold, A. L. J. Am. Chem. Soc. 1998, 120, 11834-11835.
13. (b) Farrell, J. R.; Mirkin, C. A.; Guzei, I. A.; Liable-Sands, L. M.; Rheingold, A. L. Angew. Chem., Int. Ed. 1998, 37, 465-467.
14. (c) Farrell, J. R.; Eisenberg, A. H.; Mirkin, C. A.; Guzei, I. A.; Liable-Sands, L. M.; Incarvito, C. D.; Rheingold, A. L.; Stern, C. L. Organometallics 1999, 18, 4856-4868.
15. (d) Holliday, B. J.; Farrell, J. R.; Mirkin, C. A.; Lam, K.-C.; Rheingold, A. L. J. Am. Chem. Soc. 1999, 121, 6316-6317.
16. (e) Dixon, F. M.; Eisenberg, A. H.; Farrell, J. R.; Mirkin, C. A.; Liable-Sands, L. M.; Rheingold, A. L. Inorg. Chem. 2000, 39, 3432-3433.
17. (f) Eisenberg, A. H.; Dixon, F. M.; Mirkin, C. A.; Stern, C. L.; Incarvito, C. D.; Rheingold, A. L. Organometallics 2001, 20, 2052-2058.
18. (g) Liu, X.; Stern, C. L.; Mirkin, C. A. Organometallics 2002, 21, 1017-1019.
19. (h) Ovchinnikov, M. V.; Holliday, B. J.; Mirkin, C. A.; Zakharov, L. N.; Rheingold, A. L. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4927-4931.
20. Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421-431.
21. Hansen, K. B.; Leighton, J. L.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 10924-10925
22. (a) Konsler, R. G.; Karl, J.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 10780-10781.
23. (b) Ready, J. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 2687-2688.
24. (c) Ready, J. M.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2002, 41, 1374-1377.
25. 2 that were highly disordered and treated as diffuse contributions using the program SQUEEZE (A. Spek; Platon Library). Additionally, the counterions were refined with a common B-F distance. The relatively large thermal parameters of the atoms in the pyridine molecule coordinated to the Zn atom appear to be related to a disorder in the alignment of the molecular plane. The atoms of the pyridine molecule were refined with isotropic thermal parameters and restrictions on the C-N and C-C distances. For additional crystallographic data. see the Supporting Information.