Mimicking the binding of glutamate to zinc in thermolysin and carboxypeptidase: The synthesis of [η3-(HCO2)BpBut,Pri]ZnCl by insertion of CO2 into a B-H bond of the bis(pyrazolyl)hydroborato zinc complex [BpBut,Pri]ZnCl

Journal of the Chemical Society - Dalton Transactions

Volumn , Issue 14, 1998, Pages 2281-2283

  Ghosh, Prasenjit ^a   Parkin, Gerard ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748472103     PISSN: 03009246     EISSN: None     Source Type: Journal    
DOI: 10.1039/a804025g     Document Type: Article

References (48)

1. For reviews on zinc enzymes, see, B. L. Vallee and D. S. Auld, Biochemistry, 1990, 29, 5647;
2. B. L. Vallee and D. S. Auld, Acc. Chem. Res., 1993, 26, 543;
3. I. Bertini, C. Luchinat, W. Maret, M. Zeppezauer (Editors), in Progress in Inorganic Biochemistry and Biophysics, Birkhauser, Boston, 1986, vol. 1;
4. B. L. Vallee and D. S. Auld, in Matrix Metalloprotinases and Inhibitors; eds. H. Birkedal-Hansen, Z. Werb, H. G. Welgus and H. E. van Wart, Gustav Fischer Verlag, New York, 1992, pp. 5-19;
5. B. L. Vallee and D. S. Auld, Biochemistry, 1993, 32, 6493;
6. J. E. Coleman, Annu. Rev. Biochem., 1992, 61, 897;
7. W. N. Lipscomb and N. Sträter, Chem. Rev., 1996, 96, 2375;
8. R. H. Holm, P. Kennepohl and E. I. Solomon, Chem. Rev., 1996, 96, 2239.
9. R. Alsfasser, S. Trofimenko, A. Looney, G. Parkin and H. Vahrenkamp, Inorg. Chem., 1991, 30, 4098;
10. A. Looney, R. Han, K. McNeill and G. Parkin, J. Am. Chem. Soc., 1993, 115, 4690.
11. R,Rt], with the 3- and 5-alkyl substitutents listed respectively as superscripts. See, S. Trofimenko, Chem. Rev., 1993, 93, 943;
12. G. Parkin, Adv. Inorg. Chem., 1995, 42, 291.
13. C. Kimblin, W. E. Allen and G. Parkin, J. Chem. Soc., Chem. Commun., 1995, 1813.
14. C. Kimblin, T. Hascall and G. Parkin, Inorg. Chem., 1997, 36, 5680.
15. P. Ghosh and G. Parkin, Chem. Commun., 1998, 413.
16. C. Dowling and G. Parkin, Polyhedron, 1996, 15, 2463.
17. Several studies concerned with modeling the function of these enzymes have been reported, although the zinc complexes used have not been structurally characterized as tetrahedral [NNO]ZnX derivatives. See, for example, (a) J. T. Groves and R. M. Dias, J. Am. Chem. Soc., 1979, 101, 1033;
18. (b) K. Ogino, K. Shindo, T. Minami, W. Tagaki and T. Eiki, Bull. Chem. Soc. Jpn., 1983, 56, 1101;
19. (c) C. C. Tang, D. Davalian, P. Huang and R. Breslow, J. Am. Chem. Soc., 1978, 100, 3918;
20. (d) D. S. Sigman and C. T. Jorgenson, J. Am. Chem. Soc., 1972, 94, 1724;
21. (e) A. Schepartz and R. Breslow, J. Am. Chem. Soc., 1987, 109, 1814.
22. For structures of carboxypeptidase, see, (a) D. C. Rees, M. Lewis and W. N. Lipscomb, J. Mol. Biol., 1983, 168, 367;
23. (b) M. F. Schmid and J. R. Herriott, J. Mol. Biol., 1976, 103, 175;
24. (c) D. W. Christianson and W. N. Lipscomb, Acc. Chem. Res., 1989, 22, 62.
25. For structures of thermolysin, see, (a) M. A. Holmes and B. W. Matthews, J. Mol. Biol., 1982, 160, 623;
26. (b) D. R. Holland, D. E. Tronrud, H. W. Pley, K. M. Flaherty, W. Stark, J. N. Jansonius, D. B. McKay and B. W. Matthews, Biochemistry, 1992, 31, 11 310;
27. (c) D. R. Holland, A. C. Hausrath, D. Juers and B. W. Matthews, Protein Science, 1995, 4, 1955;
28. (d) B. W. Matthews, Acc. Chem. Res., 1988, 21, 333.
29. W. R. Kester and B. W. Matthews, J. Biol. Chem., 1977, 252, 7704.
30. 10c.
31. C. Dowling, V. J. Murphy and G. Parkin, Inorg. Chem., 1996, 35, 2415.
32. But,Pri], see, C. Dowling, P. Ghosh and G. Parkin, Polyhedron, 1997, 16, 3469.
33. 2].
34. 2.
35. G. B. Deacon and R. J. Phillips, Coord. Chem. Rev., 1980, 33, 227.
36. -1, T = 293(2) K, R1 = 0.0558 for 3224 reflections. CCDC reference number 186/1038.
37. A. Abufarag and H. Vahrenkamp, Inorg. Chem., 1995, 34, 3279;
38. A. Abufarag and H. Vahrenkamp, Inorg. Chem., 1995, 34, 2207.
39. S. S. Tandon, S. Chander, L. K. Thompson, J. N. Bridson and V. McKee, Inorg. Chim. Acta, 1994, 219, 55.
40. T. C. Higgs and C. J. Carrano, Inorg. Chem., 1997, 36, 291;
41. T. C. Higgs and C. J. Carrano, Inorg. Chem., 1997, 36, 298.
42. For example, only one mononuclear tetrahedral zinc complex of a tridentate [NNO] ligand is listed the Cambridge Structural Database (Version 5.14).
43. See, E. J. Corey, P.-W. Yuen, F. J. Hannon and D. A. Wierda, J. Org. Chem., 1990, 55, 784.
44. W. Leitner, Coord. Chem. Rev., 1996, 153, 257 and refs. therein;
45. A. Behr, Carbon Dioxide Activation by Metal Complexes, VCH, Weinheim, 1988.
46. 24b (a) T. Wartik and R. K. Pearson, J. Inorg. Nucl. Chem., 1958, 7, 404;
47. (b) G. L. Monica, G. A. Ardizzoia, F. Cariati, S. Cenini and M. Pizzotti, Inorg. Chem., 1985, 24, 3920.
48. 2 insertion into a B-N bond, see, A. Meller and A. Ossko, Monatsh. Chem., 1972, 103, 577.