Erratum: Thioester hydrolysis reactivity of an Fe(III)Zn(II) complex (Inorganic Chemistry (2009) 48 (11352) DOI: 10.1021/ic901890d);Thioester hydrolysis reactivity of an Fe(III)Zn(II) complex

Inorganic Chemistry

Volumn 48, Issue 23, 2009, Pages 11352-11361

  Danford, James J ^a   Dobrowolski, Piotr ^a   Berreau, Lisa M ^a  

^a UTAH STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 72949122846     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic1020109     Document Type: Erratum

References (76)

1. Bertini, I.; Gray, H. B.; Stiefel, E. I.; Valentine, J. S. Biological Inorganic Chemistry: Structure and Reactivity; University Science Books: Sausalito, CA, 2007.
2. (a) Gahan, L. R.; Smith, S. J.; Neves, A.; Schenk, G. Eur. J. Inorg. Chem. 2009, 2745-2758.
3. (b) Ferreira, D. E. C.; De Almeida, W. B.; Neves, A.; Rocha, W. R. Phys. Chem. Chem. Phys. 2008, 10, 7039-7046.
4. (c) Smith, S. J.; Casellato, A.; Hadler, K. S.; Mitic, N.; Riley, M. J.; Bortoluzzi, A. J.; Szpoganicz, B.; Schenk, G.; Neves, A.; Gahan, L. R. Biol. Inorg. Chem. 2007, 12, 1207-1220.
5. (d) Mitic, N.; Smith, S. J.; Neves, A.; Guddat, L. W.; Gahan, L. R.; Schenk, G. Chem. Rev. 2006, 106, 3338-3363.
6. (e) Neves, A.; Lanznaster, M.; Bortoluzzi, A. J.; Peralta, R. A.; Casellatto, A.; Castellano, E. E.; Herrald, P.; Riley, M. J.; Schenk, G. J. Am. Chem. Soc. 2007, 129, 7486-7487.
7. (f) Lanznaster, M.; Neves, A.; Bortoluzzi, A. J.; Szpoganicz, B.; Schwingel, E. Inorg. Chem. 2002, 41, 5641-5643.
8. (g) Albedyhl, S.; Schnieders, D.; Jancso, A.; Gajda, T.; Krebs, B. Eur. J. Inorg. Chem. 2002, 1400-1409.
9. (h) Albedyhl, S.; Averbuch-Pouchot, M. T.; Belle, C.; Krebs, B.; Pierre, J. L.; Saint-Aman, E.; Torelli, S. Eur. J. Inorg. Chem. 2001, 1457-1464.
10. (a) Limphong, P.; McKinney, R. M.; Adams, N. E.; Bennett, B.; Makaroff, C. A.; Gunasekera, T.; Crowder, M. W. Biochemistry 2009, 48, 5426-5434.
11. (b) Campos-Bermudez, V. A.; Leite, N. R.; Krog, R.; Costa-Filho, A. J.; Soncini, F. C.; Olivia, G.; Vila, A. J. Biochemistry 2007, 46, 11069-11079.
12. (c) Marasinghe, G. P. K.; Sander, I. M.; Bennett, B.; Periyannan, G.; Yang, K.-W.; Makaroff, C. A.; Crowder, M. W. Biol. Chem. 2005, 280, 40668-40675.
13. (d) Wenzel, N. F.; Carenbauer, A. L.; Pfiester, M. P.; Schilling, O.; Meyer-Klaucke, W; Makaroff, C. A.; Crowder, M. W. J. Biol. Inorg. Chem. 2004, 9, 429-438.
14. (e) Schilling, O.; Wenzel, N.; Naylor, M.; Vogel, A.; Crowder, M.; Makaroff, C.; Meyer-Klaucke, W. Biochemistry 2003, 42, 11777-11786.
15. (f) Zang, T. M.; Hollman, D. A.; Crawford, P. A.; Crowder, M. W.; Makaroff, C. A. J. Biol. Chem. 2001, 276, 4788-4795.
16. (a) Daiyasu, H.; Osaka, K.; Ishino, Y.; Toh, H. FEBS Lett. 2001, 503, 1-6.
17. (b) Aravind, L. In Silico Biol. 1999, 1, 69-91.
18. Thornalley, P. J. Mol. Aspects Med. 1993, 14, 287-371.
19. Vander Jagt, D. L.; Hunsaker, L. A. Chem.-Biol. Interact. 2003, 143, 341-351.
20. Thornalley, P. J. Rev. Oncol. Hematol. 1995, 20, 99-128.
21. Thornalley, P. J. Amino Acids 1994, 6, 15-23.
22. Vander Jagt, D. L. Biochem. Soc. Trans. 1993, 21, 522-527.
23. (a) Mannervik, B. Drug. Metabol. Drug. Interact. 2008, 23, 13-27.
24. (b) Sukdeo, N.; Honek, J. F. Drug Metabol. Drug. Interact. 2008, 23, 29-50.
25. Chyan, M. K.; Elia, A. C.; Principato, G. B.; Giovannini, E.; Rosi, G.; Norton, S. J. Enzyme Protein 1995, 48, 164-173.
26. (a) Yang, K. W.; Sobieski, D. N.; Carenbauer, A. L.; Crawford, P. A.; Makaroff, C. A.; Crowder, M. W. Arch. Biochem. Biophys. 2003, 414, 271-278.
27. (b) Elia, A. C.; Chyan, M. K.; Principato, G. B.; Giovannini, E.; Rosi, G.; Norton, S. J. Biochem. Mol. Biol. Int. 1995, 35, 763-771.
28. (c) Murthy, N. S.; Bakeris, T.; .Kavarana, M. J.; Hamilton, D. S.; Lan, Y.; Creighton, D. J. J. Med. Chem. 1994, 37, 2161-2166.
29. (d) Norton, S. J.; Elia, A. C.; Chyan, M. K.; Gillis, G.; Frenzel, C.; Principato, G. B. Biochem. Soc. Trans. 1993, 21, 545-549.
30. (e) More, S. S.; Vince, R. J. Med. Chem. 2009, 52, 4650-4656.
31. (f) Atanasiu, V.; Stoian, I.; Manolescu, B.; Lupescu, O. Rev. Roum. Chim. 2006, 51, 861-869.
32. (g) Kalsi, A.; Kavarana, M. J.; Lu, T.; Whalen, D. L.; Hamilton, D. S.; Creighton, D. J. J. Med. Chem. 2000, 43, 3981-3986.
33. (h) Tew, K. D. Drug Resist. Updates 2000, 3, 263-264.
34. (i) Vince, R.; Brownell, J.; Akella, L. B. Bioorg. Med. Chem. Lett. 1999, 9, 853-856.
35. (j) Kavarana, M. J.; Kovaleva, E. G.; Creighton, D. J.; Wollman, M. B.; Eiseman, J. L. J. Med. Chem. 1999, 42, 221-228.
36. (a) Cameron, A. D.; Riaderström, M.; Olin, B.; Mannervik, B. Structure 1999, 7, 1067-1078.
37. (b) Crowder, M. A.; Maiti, M. K.; Banovic, L.; Makaroff, C. A. FEBS Lett. 1997, 418, 351-354.
38. O'Young T.; Sukdeo, N.; Honek, J. F. Arch. Biochem. Biophys. 2007, 459, 20-26.
39. Berreau, L. M.; Saha, A.; Arif, A. M. Dalton Trans. 2006, 183-192.
40. Armarego, W. L. F.; Perrin, D. D. of Laboratory Chemicals, 4th ed.; Butterworth-Heinemann: Boston, MA, 1996.
41. Szajna, E.; Dobrowolski, P.; Fuller, A. L.; Berreau, L. M. Inorg. Chem. 2004, 43, 3988-3997.
42. Borovik, A. S.; Papaefthymiou, V.; Taylor, L. F.; Anderson, O. P.; Que, L., Jr. J. Am. Chem. Soc. 1989, 111, 6183-6195.
43. Carvalho, N. M. F.; Horn, A., Jr.; Bortoluzzi, A. J.; Drago, V.; Antunes, O. A. C. Inorg. Chim. Acta 2006, 359, 90-98.
44. Neves, A.; de Brito, M. A.; Vencato, I.; Drago, V.; Griesar, K.; Haase, W. Inorg. Chem. 1996, 35, 2360-2368.
45. (a) Russell, G. A.; Mikol, G. J. J. Am. Chem. Soc. 1966, 88, 5498-5504.
46. (b) Hall, S. S.; Poet, A. Tetrahedron Lett. 1970, 2867-2868.
47. 1 ligand has been previously synthesized (Lambert, E.; Chabut, B.; Chardon-Noblat, S.; Deronzier, A.; Chottard, G.; Bousseksou, A.; Tuchagues, J.-P.; Laugier, J.; Bardet, M.; Latour, J.-M. J. Am. Chem. Soc. 1997, 119, 9424-9437). The procedure reported herein reduces the overall number of steps required for the preparation of this ligand.
48. Wolsey, W. C. Chem. Educ. 1973, 50, A335-A337.
49. Ming, L.-J.; Jang, H. G.; Que, L., Jr. Inorg. Chem. 1992, 31, 359-364.
50. Berreau, L. M. Adv. Phys. Org. Chem. 2006, 41, 79-181.
51. 2O; Cadogan, J. I. G.; Buckingham, J.; MacDonald, F. J.; Rhodes, P. H. Dictionary of Organic Compounds, 6th ed.; CRC Press: Boca Raton, FL, 1996.
52. Serjeant, E. P.; Dempsey, B. Ionization Constants of Organic Acids in Aqueous Solution; Pergamon: Oxford, U.K., 1979.
53. Aoyama, T.; Takido, T.; Kodomari, M. Synth. Commun. 2003, 33, 3817-3824.
54. See for example: Zhao, H.; Martin, B. M.; Bisoffi, M.; Dunaway-Mariano, D. Biochemistry 2009, 48, 5507-5509.
55. 2O; Lide, D. R. Handbook of Chemistry and Physics, 74th ed.; CRC Press: Boca Raton, FL, 1993.
56. (a) Rao, T. V.; Sain, B.; Murthy, P. S.; Rao, T. S. R. P.; Joshi, G. C.; Jain, A. K. J. Chem. Res. (S) 1997, 300-301.
57. (b) Plietker, B. Iron. Catalysis in Organic Chemistry; Wiley-VCH: Weinheim, Germany, 2008.
58. Copik, A. J.; Waterson, S.; Swierczek, S. I.; Bennett, B; Holz, R. C. Inorg. Chem. 2005, 44, 1160-1162.
59. While monodentate coordination of the deprotonated α- hydroxythioester is proposed based on the six-coordinate ligand environment of the Zn(II) center, formation of a chelate structure via interaction with the Zn(II) center and loss of another ligand (e.g., bridging hydroxide) cannot be ruled out. Chelating structures involving Zn(II)-coordination of a deprotonated α-hydroxyester have been reported.(a) Chamberlain, B. M.; Cheng, M.; Moore, D. R.; Ovitt, T. M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc 2001, 123, 3229-3238.
60. (b) Rieth, L. R.,; Moore, D. R.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2002, 124, 15239-15248.
61. Okuyama, T.; Nagamatsu, H.; Fueno, T. J. Org. Chem. 1981, 46, 1336-1342.
62. (a.) Grillo, M. A.; Colombatto, S. Amino Acids 2008, 35, 29-36.
63. (b) Thornalley, P. J. Novartis Found. Symp. 2001, 285, 229-243.
64. (c) Kalousová, M.; Zima, T.; Tesar, V.; Dusilová- Sulková, S.; Skrha, J. Mutat, Res. 2005, 579, 31-46.
65. (d) Thornalley, P. J. Biochem. Soc. Trans. 2003, 31, 1343-1348.
66. (e) Thornalley, P. J. Chem. Biol. Interact. 1998, 111-112, 137-151.
67. Rudzka, K.; Arif, A. M.;Berreau, L. M. J. Am. Chem. Soc., 2006, 128, 17018-17023.
68. We note that an Fe(III)Zn(II) form of metallo-β-lactamasc L1 has been recently reported, (a) Hu, Z.; Gunasekera, T. S.; Spadafora, L.; Bennett, B.; Crowder, M. W. Biochemistry 2008, 47, 7947-7953.
69. (b) Hu, Z.; Periyannan, G.; Bennett, B.; Crowder, M. W. J. Am. Chem. Soc. 2008, 130, 14207-14216.
70. Chen, S.-L.; Fang, W.-H.; Himo, F. J. Inorg. Biochem. 2009, 103, 274-281.
71. Bergquist, C.; Storrie, H.; Koutcher, L.; Bridgewater, B. M.; Friesner, R. A.; Parkin, G. J. Am. Chem. Soc. 2000, 122, 12651-12658.
72. Gawron, O.; Duggan, M.; Grelecki, C. J. Anal. Chem. 1952, 24, 969-970.
73. Bou-Abdallah, F.; Chasteen, N. D. J. Biol. Inorg. Chem. 2008, 13, 15-24.
74. (a) Vander Jagt, D. L. Drug. Metabol. Drug Interact. 2008, 23, 93-124.
75. (b) Kuhla, B.; Lüth, H. J.; Haferburg, D.; Boeck, K.; Arendt, T.; Münch, G. Ann. N. Y. Acad. Sci. 2005, 1043, 211-216.
76. (c) Thornalley, P. J. Drug Metabol. Drug Interact. 2008, 23, 125-150.