Synthetic modeling of zinc thiolates: Quantitative assessment of hydrogen bonding in modulating sulfur alkylation rates

Proceedings of the National Academy of Sciences of the United States of America

Volumn 100, Issue 7, 2003, Pages 3695-3700

  Chiou, Show Jen ^a   Riordan, Charles G ^a   Rheingold, Arnold L ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SULFUR; ZINC; METAL; THIOL DERIVATIVE;

ALKYLATION; ARTICLE; COMPLEX FORMATION; DNA REPAIR; ENZYME ACTIVATION; HYDROGEN BOND; HYDROLYSIS; HYDROPHILICITY; LIGAND BINDING; MODEL; MOLECULAR INTERACTION; PRIORITY JOURNAL; SYNTHESIS; TRANSCRIPTION REGULATION; CHEMICAL STRUCTURE; CHEMISTRY; KINETICS;

ALKYLATION; HYDROGEN BONDING; KINETICS; METALS; MODELS, MOLECULAR; SULFHYDRYL COMPOUNDS; ZINC;

EID: 0037389593     PISSN: 00278424     EISSN: None     Source Type: Journal    
DOI: 10.1073/pnas.0637221100     Document Type: Article

References (41)

1. Lipscomb, W. N. & Sträter, N. (1996) Chem. Rev. 96, 2375-2434.
2. Berg, J. M. & Godwin, H. A. (1997) Annu. Rev. Biophys. Biomol. Struct. 26, 357-371.
3. Wilcox, D. E. (1996) Chem. Rev. 96, 2435-2458.
4. Matthews, R. G. & Goulding, C. W. (1997) Curr. Opin. Chem. Biol. 1, 332-339.
5. Hightower, K. E. & Fierke, C. A. (1999) Curr. Opin. Chem. Biol. 3, 176-181.
6. Penner-Hahn, J. E. (2002) Indian J. Chem. A 41, 13-21.
7. Ermler, U., Grabarse, W., Shima, S., Goubeaud, M. & Thauer, R. K. (1997) Science 278, 1457-1462.
8. Lin, Y. X., Dotsch, V., Wintner, T., Peariso, K., Myers, L. C., Penner-Hahn, J. E., Verdine, G. L. & Wagner, G. (2001) Biochemistry 40, 4261-4271.
9. Evans, J. C., Huddler, D. P., Jiracek, J., Castro, C., Millian, N. S., Garrow, T. A. & Ludwig, M. L. (2002) Structure 10, 1159-1171.
10. Krum, J. G., Ellsworth, H., Sargeant, R. R., Rich, G. & Ensign, S. A. (2002) Biochemistry 41, 5005-5014.
11. Matthews, R. G. (2001) Acc. Chem. Res. 34, 681-689.
12. Peariso, K., Zhou, Z. H. S., Smith, A. E., Matthews, R. G. & Penner-Hahn, J. E. (2001) Biochemistry 40, 987-993.
13. Wilker, J. J. & Lippard, S. J. (1997) Inorg. Chem. 36, 969-978.
14. Wilker, J. J. & Lippard, S. J. (1995) J. Am. Chem. Soc. 117, 8682-8683.
15. Warthen, C. R., Hammes, B. S., Carrano, C. J. & Crans, D. C. (2001) J. Biol. Inorg. Chem. 6, 82-90.
16. Brand, U., Rombach, M., Seebacher, J. & Vahrenkamp, H. (2001) Inorg. Chem. 40, 6151-6157.
17. Grapperhaus, C. A., Tuntulani, T., Reibenspies, J. H. & Darensbourg, M. Y. (1998) Inorg. Chem. 37, 4052-4058.
18. Bridgewater, B. M., Fillebeen, T., Friesner, R. A. & Parkin, G. (2000) J. Chem. Soc. Dalton Trans., 4494-4496.
19. Roehm, P. C. & Berg, J. M. (1998) J. Am. Chem. Soc. 120, 13083-13087.
20. Chiou, S.-J., Innocent, J., Lam, K.-C., Riordan, C. G., Liable-Sands, L. & Rheingold, A. L. (2000) Inorg. Chem. 39, 4347-4353.
21. Ohrenberg, C., Ge, P., Schebler, P., Riordan, C. G., Yap, G. P. A. & Rheingold, A. L. (1996) Inorg. Chem. 35, 749-754.
22. Chiou, S.-J., Ge, P., Riordan, C. G., Liable-Sands, L. & Rheingold, A. L. (1999) Chem. Commun., 159-160.
23. MacBeth, C. E., Golombek, A. P., Young, V. G., Yang, C., Kuczera, K., Hendrich, M. P. & Borovik, A. S. (2000) Science 289, 938-941.
24. Momenteau, M. & Reed, C. A. (1994) Chem. Rev. 94, 659-698.
25. Huang, J., Ostrander, R. L., Rheingold, A. L., Leung, Y. C. & Walters, M. A. (1994) J. Am. Chem. Soc. 116, 6769-6776.
26. Okamura, T., Takamizawa, S., Ueyama, N. & Nakamura, A. (1998) Inorg. Chem. 37, 18-28.
27. Walters, M. A., Dewan, J. C., Min, C. & Pinto, S. (1991) Inorg. Chem. 30, 2656-2662.
28. Smith, J. N., Shirin, Z. & Carrano, C. J. (2003) J. Am. Chem. Soc. 125, 868-869.
29. Ueno, T., Inohara, M., Ueyama, N. & Nakamura, A. (1997) Bull. Chem. Soc. Jpn. 70, 1077-1083.
30. Espenson, J. H. (1995) Chemical Kinetics and Reaction Mechanisms (McGrawHill, New York).
31. Hamilton, W. C. & Ibers, J. A. (1968) Hydrogen Bonding in Solids (Benjamin, New York).
32. Darensbourg, M. Y., Longridge, E. M., Payne, V., Reibenspies, J., Riordan, C. G., Springs, J. J. & Calabrese, J. C. (1990) Inorg. Chem. 29, 2721-2726.
33. McGuire, D. G., Khan, M. A. & Ashby, M. T. (2002) Inorg. Chem. 41, 2202-2208.
34. Nesloney, C. L. & Kelly, J. W. (1996) J. Am. Chem. Soc. 118, 5836-5845.
35. Gallo, E. A. & Gellman, S. H. (1993) J. Am. Chem. Soc. 115, 9774-9788.
36. Bender, B. R. (1995) J. Am. Chem. Soc. 117, 11239-11246.
37. Bender, B. R., Kubas, G. J., Jones, L. H., Swanson, B. I., Eckert, J., Capps, K. B. & Hoff, C. D. (1997) J. Am. Chem. Soc. 119, 9179-9190.
38. Crabtree, R. H. (1993) Angew. Chem. Int. Ed. Engl. 32, 789-805.
39. Myers, L. C., Terranova, M. P., Ferentz, A. E., Wagner, G. & Verdine, G. L. (1993) Science 261, 1164-1167.
40. Bakbak, S., Incarvito, C. D., Rheingold, A. L. & Rabinovich, D. (2002) Inorg. Chem. 41, 998-1001.
41. Kimblin, C., Murphy, V. J., Hascall, T., Bridgewater, B. M., Bonanno, J. B. & Parkin, G. (2000) Inorg. Chem. 39, 967-974.