Protonation of the hydroxide ligand in a synthetic analogue of carbonic anhydrase, [Tp(Bu(t),Me)]ZnOh: Inhibition of reactivity towards CO2 [9]

Journal of the American Chemical Society

Volumn 121, Issue 26, 1999, Pages 6322-6323

  Bergquist, Catherine ^a   Parkin, Gerard ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

CARBONATE DEHYDRATASE; HYDROXIDE; ZINC;

ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME CONFORMATION; ENZYME SYNTHESIS; LETTER; PROTON TRANSPORT; STRUCTURE ACTIVITY RELATION;

EID: 0033532885     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja991134j     Document Type: Letter

References (52)

1. See, for example: (a) Holm, R. H.; Kennepohl, P.; Solomon, E. I. Chem. Rev. 1996, 96, 2239-2314.
2. (b) Lipscomb, W. N.; Sträter, N. Chem. Rev. 1996, 96, 2375-2433.
3. (c) Kimura, E.; Koike, T.; Shionoya, M. Struct. Bonding 1997, 89, 1-28.
4. (d) Lindskog, S. Pharmacol. Ther. 1997, 74, 1-20.
5. For calculations of the pK, of zinc aqua complexes in model systems, see: Bertini, I.; Luchinat, C.; Rosi, M.; Sgamellotti, A.; Tarantelli, F. Inorg. Chem. 1990, 29, 1460-1463.
6. Alsfasser, R.; Trofimenko, S.; Looney, A.; Parkin, G.; Vahrenkamp, H. Inorg. Chem. 1991, 30, 4098-4100.
7. Ruf, M.; Vahrenkamp, H. Inorg. Chem. 1996, 35, 6571-6578.
8. Kimblin, C.; Allen, W. E.; Parkin, G. J. Chem. Soc., Chem. Commun. 1995, 1813-1815.
9. 4). See: Kimura, E.; Shiota, T.; Koike, T.; Shiro, M.; Kodama, M. J. Am. Chem. Soc. 1990, 112, 5805-5811.
10. - sources. See, for example: Parkin, G. Adv. Inorg. Chem. 1995, 42, 291-393.
11. (a) Hartmann, U.; Vahrenkamp, H. Chem. Ber. 1994, 127, 2381-2385.
12. (b) Ruf, M.; Weis, K.; Vahrenkamp, H. J. Chem. Soc., Chem. Commun. 1994, 135-136.
13. (c) Brandsch, T.; Schell, F.-A.; Weis, K.; Ruf, M.; Müller, B.; Vahrenkamp, H. Chem. Ber./Recueil 1997, 130, 283-289.
14. (d) Ruf, M.; Weis, K.; Brasack, I.; Vahrenkamp, H. Inorg. Chim. Acta 1996, 250, 271-281.
15. (e) Ruf, M.; Weis, K.; Vahrenkamp, H. Inorg. Chem. 1997, 36, 2130-2137.
16. (f) Hikichi, S.; Tanaka, M.; Moro-oka, Y.; Kitajima, N. J. Chem. Soc., Chem. Commun. 1992, 814-815.
17. 9c,d (a) Bradley, D. C.; Harding, I. S.; Keefe, A. D.; Motevalli, M.; Zheng, D. H. J. Chem. Soc., Dalton Trans. 1996, 3931-3936.
18. (b) Harlan, C. J.; Bergquist, C.; Bridgewater, B. M.; Norton, J. R.; Parkin, G., unpublished results.
19. (c) Siedle, A. R.; Lamanna, W. M.; Newmark, R. A.; Stevens, J.; Richardson, D. E.; Ryan, M. Makromol. Chem., Macromol. Symp. 1993, 66, 215-224.
20. (d) Danopoulos, A. A.; Galsworthy, J. R.; Green, M. L. H.; Cafferkey, S.; Doerrer, L. H.; Hursthouse, M. B. J. Chem. Soc., Chem. Commun. 1998, 2529-2530.
21. 10c (a) References 9c and 9d.
22. (b) Hill, G. S.; Manojlovic-Muir, L.; Muir, K. W.; Puddephatt, R. J. Organometallics 1997, 16, 525-530.
23. (c) Shaffer, T. D.; Ashbaugh, J. R. J. Polym. Sci.: Part A: Polym. Chem. 1997, 35, 329-344.
24. 3, see: Piers, W. E.; Chivers, T. Chem. Soc. Rev. 1997, 26, 345-354.
25. But,Me]ZnI has been previously described. See: Looney, A. Ph.D. Thesis, Columbia University, 1993.
26. 2] moieties [1.871(6) - 1.916(6) A]. See: Ruf, M.; Weis, K.; Vahrenkamp, H. J. Am. Chem. Soc. 1996, 118, 9288-9294.
27. 2 is 2.011(3) Å. See ref 8c.
28. 15b (a) Reference 9d.
29. (b) Janiak, C.; Braun, L.; Scharmann, T. G.; Girgsdies, F. Acta Crystallogr. 1998, C54, 1722-1724.
30. 16d (a) Schaefer, W. P.; Quan, R. W.; Bercaw, J. E. Acta Crystallogr. 1993, C49, 878-881.
31. (b) Siedle, A. R.; Newmark, R. A.; Lamanna, W. M.; Huffman, J. C. Organometallics 1993, 12,1491-1492.
32. 3BOH] due to a typographic error (Huffman, J. C., personal communication).
33. (d) Reference 9d.
34. 17b (a) Reference 10b.(b) Reference 9d.
35. 2 [1.52(1) Å]. See: Parks, D. J.; Piers, W. E.; Parvez, M.; Atencio, R.; Zaworotko, M. J. Organometallics 1998, 17, 1369-1377.
36. -, see: Ardon, M.; Bino, A. Struct. Bonding 1987, 65, 1-28.
37. 2] moieties, see ref 13.
38. In addition, the zinc-bound water is also part of a hydrogen-bonding network involving additional water molecules which mediate a proton shuttle to His-64, prior to proton transfer to the surroundings. See: (a) Denisov, V. P.; Jonsson, B.-H.; Halle, B. J. Am. Chem. Soc. 1999, 121, 2327-2328.
39. (b) Toba, S.; Colombo, G.; Merz, K. M., Jr. J. Am. Chem. Soc. 1999, 121, 2290-2302.
40. (c) Christianson, D. W.; Fierke, C. A. Acc. Chem. Res. 1996, 29, 331-339 and references therein.
41. (d) Liang, Z.; Xue, Y.; Behravan, G.; Jonsson, B.-H.; Lindskog, S. Eur. J. Biochem. 1993, 211, 821-827.
42. (e) Merz, K. M., Jr. J. Mol. Biol. 1990, 214, 799-802.
43. (f) Eriksson, A. E.; Jones, A. T.; Liljas, A. Proteins 1988, 4, 274-282.
44. (g) Xue, Y.; Liljas, A.; Jonsson, B.-H.; Lindskog, S. Proteins 1993, 17, 93-106.
45. (h) Håkansson, K.; Carlsson, M.; Svensson, L. A.; Liljas, A. J. Mol. Biol. 1992, 227, 1192-1204.
46. Zhang, X.; Hubbard, C. D.; van Eldik, R. J. Phys. Chem. 1996, 100, 9161-9171.
47. 2 by certain macrocyclic zinc complexes, nevertheless, suggests that the reactions proceed via initial deprotonation of a zinc-bound water. See, for example: (a) Zhang, X.; van Eldik, R. Inorg. Chem. 1995, 34, 5606-5614.
48. (b) Zhang, X.; van Eldik, R.; Koike, T.; Kimura, E. Inorg. Chem. 1993, 32, 5749-5755.
49. 24b (a) Nakata K.; Uddin M. K.; Ogawa, K.; Ichikawa, K. Chem. Lett. 1997, 991-992.
50. (b) Reference 8c.
51. Looney, A.; Han, R.; McNeill, K.; Parkin, G. J. Am. Chem. Soc. 1993, 115, 4690-4697.
52. But,Me]ZnOH.