Polyaza[n]paracyclophanes as synthetic models of Zn containing enzymes. The role of a non coordinated nitrogen atom in the proximity of the metal

Tetrahedron

Volumn 53, Issue 13, 1997, Pages 4751-4762

  Altava, Belen ^a   Burguete, M Isabel ^a   Luis, Santiago V ^a   Miravet, Juan F ^a   García España, Enrique ^b   Marcelino, Victor ^b   Soriano, Conxa ^b  

^a UNIVERSITAT JAUME I   (Spain)

^b UNIVERSITY OF VALENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ENZYME; MACROCYCLIC COMPOUND;

ARTICLE; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; MODEL; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0030964389     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00144-0     Document Type: Article

References (64)

1. a) Neuberger, A.; Brocklehurst, K., Eds. Hydrolytic Enzymes, Elsevier, Amsterdam, 1987.
2. b) Bertini, I.; Luchinat, C.; Maret, W.; Zeppesauer, M, Eds. Zinc Enzymes Brikäuser, Boston, 1986.
3. Matthews, B.W. Acc. Chem. Res. 1988, 21, 333-340.
4. Bertini, I.; Gray; H.B.; Lippard, S.J.; Valentine, J.S. Bioinorganic Chemistry University Science Books, Mill Valley, 1994.
5. a) Kimura, E. Pure Appl. Chem. 1993, 65, 355-359.
6. b) Kimura, E. Progress Inorg. Chem. 1994, 41, 443-491.
7. b) Vallee, B.L.; Auld, D.S. Acc. Chem. Res. 1993, 26, 543-551.
8. Breslow, R. Acc. Chem. Res. 1995, 28, 146-153.
9. Silverman, D.N.; Lindskog, S. Acc. Chem. Res. 1988, 21, 30-36.
10. a) Zheng, Y.-J.; Merz, K.M., Jr. J. Am. Chem. Soc. 1992, 114, 10498-10507, and references therein.
11. b) Åqvist, J.; Fothergill, M.; Warshel, A. J. Am. Chem. Soc. 1993, 115, 631-635.
12. a) Kiefer, L.L.; Paterno, S.A.; Fierke, C.A. J. Am. Chem. Soc. 1995, 117, 6831-6837.
13. b) Lesburg, C.A.; Christianson, D.W. J. Am. Chem. Soc. 1995, 117, 6838-6844.
14. Christianson, D.W.; Fierke, C.A. Acc. Chem. Res. 1996, 29, 331-339.
15. a) Jain, A.; Huang, S.G.; Whitesides, G.M. J. Am. Chem. Soc. 1994, 116, 5057-5062.
16. b) Cappalonga Bunn, A.M.; Alexander, R.S.; Christianson, D.W. J. Am. Chem. Soc. 1994, 116, 5063-5068.
17. Chin, D.N.; Whitesides, G.M. J. Am. Chem. Soc. 1995, 117, 6153-6164.
18. Cheng, X.; Chen, R.; Bruce, J.E.; Schwartz, B.L; Anderson, G.A.; Hofstadler, S.A.; Gale, D.C.; Smith, R.D.; Gao, J.; Sigal, G.B.; Mammen, M.; Whitesides, G.M. J. Am. Chem. Soc. 1995, 117, 8859-8860.
19. a) Tang, C.C.; Davalian, D.; Huang, P.; Breslow, R. J. Am. Chem. Soc. 1978, 100, 3918-3922.
20. b) Breslow, R.; Hunt, J.T.; Smiley, R.; Tarnowski, T. J. Am. Chem. Soc. 1983, 105, 5337-5342.
21. a) Slebocka-Tilk, H.; Cocho, J.L.; Frakman, Z.; Brown, R:S. J. Am. Chem. Soc. 1984, 106, 2421-2431.
22. b) Brown, R.S.; Zamkanei, M.; Cocho, J.L. J. Am. Chem. Soc. 1984, 106, 5222-5228.
23. c) Jairam, R.; Potvin, P.G. J. Org. Chem. 1992, 57, 4136-4141.
24. For models based on tris(pyrazolyl)borate see also: d) Kitajima, N.; Hikichi, S.; Tanaka, M.; Moro-oka, Y. J. Am. Chem. Soc. 1993, 115, 5496-5508.
25. e) Looney, A.; Han, R.; McNeill, K.; Parkin, G. J. Am. Chem. Soc. 1993, 115, 4690-4697.
26. Wooley, P. Nature 1975, 258, 677-682.
27. a) Gellman, S.; Petter, R.; Breslow, R. J. Am. Chem. Soc., 1986, 108, 2388-2394.
28. b) Breslow, R.; Singh, S. Bioorg. Chem. 1988, 16, 408-417.
29. a) Kimura, E.; Shiota, T.; Koike, T.; Shiro, M.; Kodama, M. J. Am. Chem. Soc. 1990, 112, 5805-5811.
30. b) Koike, T.; Kimura, E.; Nakamura, I.; Hashimoto, Y., Shiro, M. J. Am. Chem. Soc. 1992, 114, 7338-7345.
31. Zhang, X.; van Eldik, R.M; Koike, T.; Kimura, E. Inorg. Chem., 1993, 32, 5749-5755.
32. Kimura, E.; Nakamura, I.; Koike, T.; Shionoya, M.; Kodama, Y.; Ikeda, T.; Shiro, M. J. Am. Chem. Soc. 1994, 116, 4764-4771.
33. e) Koike, T.; Kajitani, S.; Nakamura, I.; Kimura, E., Shiro, M. J. Am. Chem. Soc. 1995, 117, 1210-1219.
34. a) Andrés, A.; Burguete, M.I.; García-España, E.; Luis, S.V.; Miravet, J.F.; Soriano, C. J. Chem. Soc., Perkin Trans. 2 1993, 749-755.
35. b) Bencini, A.; Burguete, M.I.; García-España, E.; Luis, S.V.; Miravet, J.F.; Soriano, C. J. Org. Chem. 1993, 58, 4749-4753.
36. Bianchi, A.; Escuder, B.; García-España, E.; Luis, S.V.; Marcelino, V.; Miravet, J.F.; Ramírez, J.A. J. Chem. Soc., Perkin Trans. 2 1994, 1253-1259.
37. a) Doménech, A.; Folgado, J. V.; García-España, E.; Luis, S.V.; Llinares, J.-M.; Miravet, J.F.; Ramírez, J. A. J. Chem. Soc., Dalton Trans. 1995, 541-547.
38. b) García-España, E.; Latorre, J.; Luis, S.V.; Miravet, J.F.; Pozuelo, P.; Ramírez, J. A.; Soriano, C. Inorg. Chem. 1996, 35, 4591-4596.
39. Burguete, M.I.; Escuder, B; Luis, S.V.; Miravet, J.F. .; García-España, E. Tetrahedron Lett. 1994, 35, 9075-9078.
40. a) Kemp, D.S.; Petrakis, K.S. J. Org. Chem. 1981, 46, 5140-5143.
41. b) for receptors based on Kemp's triacid see: Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1990, 29, 245-255.
42. For the interaction of Kemp's anions with polyammonium receptors see: Bencini, A.; Bianchi, A.; Burguete, M.I.; García-España, E.; Luis, S.V.; Ramírez, J.A. J. Am. Chem. Soc. 1992, 114, 1919-1920.
43. a) Mertes, K.B.; Mertes, M.P. Acc. Chem. Res. 1990, 23, 413-418.
44. b) Papoyan, G.; Gu, K.-J.; Wiorkiewicz, J.; Kuczera, K.; Mertes, K.B. J. Am. Chem. Soc. 1996, 118, 1354-1364.
45. a) Chin, J. Acc. Chem. Res. 1991, 24, 145-152.
46. b) Suh, J. Acc. Chem. Res. 1992, 25, 273-279.
47. Tsao, B.L.; Pieters, R.J.; Rebek, J. J. Am. Chem. Soc. 1995, 117, 2210-2213.
48. For catalytic systems based on synthetic cyclophanes see, for instance: a) Murakami, Y. Top. Curr. Chem. 1983, 115, 107-155.
49. b) Tabushi, I.; Yamamura, K. Top. Curr. Chem. 1983, 113, 145-182.
50. Murakami, Y. Inclusion Phenomena and Molecular Recognition, J. Atwood, ed.; Plenum Press, New York, 1990, pp 107-117.
51. Altava, B.; Bianchi, A.; Bazzicalupi, C.; Burguete, M.I.; García-España, E.; Luis, S.V.; Miravet, J.F. Supramolecular Chem. in press.
52. Nair, S.K.; Christianson, D. J. Am. Chem. Soc. 1991, 113, 9455-9458.
53. H3L 4.69 (3).
54. For an interesting analysis of how structural changes affect zinc-water acidity in Zn-polyamine complexes see: Canary, J.W.; Xu, J.; Castagnetto, J.M.; Rentzeperis, D.; Marky, L.A. J. Am. Chem. Soc. 1995, 117, 11545-11547.
55. Mohamadi, F.; Richards, N.G.J.; Guida, W.C.; Liskamp, R.; Caufield, C.; Chang, G.; Hendrikson, T.; Still, W.C. J. Comput. Chem. 1990, 11, 440-467.
56. Spartan 3.1, Wavefunction, Inc., Irvine, CA.
57. Micheloni, M.; May, P.; Williams, D. R. J. Inorg. Nucl. Chem. 1978, 40, 1209-1219.
58. Micheloni, M.; Sabatini, A.; Vacca, A. Inorg. Chim. Acta. 1977, 25, 41-48.
59. García-España, E.; Ballester, M.-J.; Lloret, F.; Moratal, J.-M.; Faus, J.; Bianchi, A. J. Chem. Soc., Dalton Trans. 1988, 101-104.
60. Fontanelli, M.; Micheloni, M. Proceedings of the 1 Spanish-Italian Congress on Thermodynamics of Metal Complexes Peñíscola, Castellón, Spain, 1990.
61. Gran G. Analyst (London) 1952, 77, 661-671;
62. Rossotti, F. J.; Rossotti, H. J. Chem. Educ. 1965, 42, 375-378.
63. Gans, P.; Sabatini, A.; Vacca, A. J. Chem. Soc., Dalton Trans. 1985, 1195-1200.
64. Vacca, A. Unpublished work.