The Uracil C(5) Position as a Metal Binding Site: Solution and X-ray Crystal Structure Studies of PtII and HgII Compounds

Inorganic Chemistry

Volumn 35, Issue 2, 1996, Pages 397-403

  Höpp, Markus ^a   Erxleben, Andrea ^a   Rombeck, Ingo ^a   Lippert, Bernhard ^a  

^a TU DORTMUND UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0040159273     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic950842c     Document Type: Article

References (61)

1. Lusty, J. R., Ed. CRC Handbook of Nucleobase Complexes; CRC Press: Boca Raton, FL. 1990; Vol. I.
2. (a) Dale, R. M. K.; Livingston, D. C.; Ward, D. C. Proc. Natl. Acad. Sci. U.S.A. 1973, 70, 2238.
3. (b) Dale, R. M. K.; Martin, E.; Livingston, D. C.; Ward, D. C. Biochemistry 1975, 14, 2447.
4. (c) Dale, R. M. K.; Ward, D. C. Biochemistry 1975, 14, 2458.
5. Mansy, S.; Tobias, R. S. Inorg. Chem. 1975, 14, 287.
6. Krentzien, H.; Clarke, M. J.; Taube, H. Biomorg. Chem. 1975, 4, 143.
7. Johnson, A.; O'Connell, L. A.; Clarke, M. J. Inorg. Chim. Acta 1993, 210, 151.
8. (a) Konmair, N.; Beck, W. Chem. Ber. 1976, 109, 970.
9. (b) Buncel, E.; Norris, A. R.; Racz, W. J.; Taylor, S. E. J. Chem. Soc., Chem. Commun. 1979, 562.
10. (c) Norris, A. L.; Kumar, R. Inorg. Chim. Acta 1984, 93, 33.
11. Schöllhorn, H.; Thewalt, U.; Lippert, B. J. Chem. Soc., Chem. Commun. 1986, 258.
12. Zhang, S.; Shepherd, R. E. Inorg. Chim. Acta 1989, 163, 237.
13. (a) Zhang, S.; Holl, L. A.; Shepherd, R. E. Inorg. Chem. 1990, 29, 1012.
14. (b) Shepherd, R. E.; Zhang, S.; Lin, F.-T.; Kortes, R. A. Inorg. Chem. 1992, 31, 1457.
15. See, e.g.: (a) Jaouen, G.; Vessières, A.; Butler, I. S. Acc. Chem. Res. 1993, 26, 361. (b) Sheldrick, W. S.; Hagen-Eckhard, H. S.; Heeb, S. Inorg. Own. Acta 1993, 206, 15. Smith, D. P.; Kohen, E.; Maestre, M. F.; Fish, R. H. Inorg. Chem. 1993, 32, 4119. Smith, D. P.; Griffin, M. T.; Olmstead, M. M ; Maestre, M F.; Fish, R. H. Inorg. Chem. 1993, 32, 4677. (e) Krämer, R.; Polborn, K.; Robl, C.; Beck, W. Inorg. Chim. Acta 1992, 198-200, 415. (f) Ryabov, A. D. Angew. Chem., Int. Ed. Engl. 1991, 30, 931. (g) Kuo, L. Y.; Kanatzidis, M. G.; Sabat, M.; Tipton, A. L.; Marks, T. J. J. Am. Chem. Soc. 1991, 113, 9027.
16. See, e.g.: (a) Jaouen, G.; Vessières, A.; Butler, I. S. Acc. Chem. Res. 1993, 26, 361. (b) Sheldrick, W. S.; Hagen-Eckhard, H. S.; Heeb, S. Inorg. Own. Acta 1993, 206, 15. Smith, D. P.; Kohen, E.; Maestre, M. F.; Fish, R. H. Inorg. Chem. 1993, 32, 4119. Smith, D. P.; Griffin, M. T.; Olmstead, M. M ; Maestre, M F.; Fish, R. H. Inorg. Chem. 1993, 32, 4677. (e) Krämer, R.; Polborn, K.; Robl, C.; Beck, W. Inorg. Chim. Acta 1992, 198-200, 415. (f) Ryabov, A. D. Angew. Chem., Int. Ed. Engl. 1991, 30, 931. (g) Kuo, L. Y.; Kanatzidis, M. G.; Sabat, M.; Tipton, A. L.; Marks, T. J. J. Am. Chem. Soc. 1991, 113, 9027.
17. See, e.g.: (a) Jaouen, G.; Vessières, A.; Butler, I. S. Acc. Chem. Res. 1993, 26, 361. (b) Sheldrick, W. S.; Hagen-Eckhard, H. S.; Heeb, S. Inorg. Own. Acta 1993, 206, 15. Smith, D. P.; Kohen, E.; Maestre, M. F.; Fish, R. H. Inorg. Chem. 1993, 32, 4119. Smith, D. P.; Griffin, M. T.; Olmstead, M. M ; Maestre, M F.; Fish, R. H. Inorg. Chem. 1993, 32, 4677. (e) Krämer, R.; Polborn, K.; Robl, C.; Beck, W. Inorg. Chim. Acta 1992, 198-200, 415. (f) Ryabov, A. D. Angew. Chem., Int. Ed. Engl. 1991, 30, 931. (g) Kuo, L. Y.; Kanatzidis, M. G.; Sabat, M.; Tipton, A. L.; Marks, T. J. J. Am. Chem. Soc. 1991, 113, 9027.
18. See, e.g.: (a) Jaouen, G.; Vessières, A.; Butler, I. S. Acc. Chem. Res. 1993, 26, 361. (b) Sheldrick, W. S.; Hagen-Eckhard, H. S.; Heeb, S. Inorg. Own. Acta 1993, 206, 15. Smith, D. P.; Kohen, E.; Maestre, M. F.; Fish, R. H. Inorg. Chem. 1993, 32, 4119. Smith, D. P.; Griffin, M. T.; Olmstead, M. M ; Maestre, M F.; Fish, R. H. Inorg. Chem. 1993, 32, 4677. (e) Krämer, R.; Polborn, K.; Robl, C.; Beck, W. Inorg. Chim. Acta 1992, 198-200, 415. (f) Ryabov, A. D. Angew. Chem., Int. Ed. Engl. 1991, 30, 931. (g) Kuo, L. Y.; Kanatzidis, M. G.; Sabat, M.; Tipton, A. L.; Marks, T. J. J. Am. Chem. Soc. 1991, 113, 9027.
19. See, e.g.: (a) Jaouen, G.; Vessières, A.; Butler, I. S. Acc. Chem. Res. 1993, 26, 361. (b) Sheldrick, W. S.; Hagen-Eckhard, H. S.; Heeb, S. Inorg. Own. Acta 1993, 206, 15. Smith, D. P.; Kohen, E.; Maestre, M. F.; Fish, R. H. Inorg. Chem. 1993, 32, 4119. Smith, D. P.; Griffin, M. T.; Olmstead, M. M ; Maestre, M F.; Fish, R. H. Inorg. Chem. 1993, 32, 4677. (e) Krämer, R.; Polborn, K.; Robl, C.; Beck, W. Inorg. Chim. Acta 1992, 198-200, 415. (f) Ryabov, A. D. Angew. Chem., Int. Ed. Engl. 1991, 30, 931. (g) Kuo, L. Y.; Kanatzidis, M. G.; Sabat, M.; Tipton, A. L.; Marks, T. J. J. Am. Chem. Soc. 1991, 113, 9027.
20. See, e.g.: (a) Jaouen, G.; Vessières, A.; Butler, I. S. Acc. Chem. Res. 1993, 26, 361. (b) Sheldrick, W. S.; Hagen-Eckhard, H. S.; Heeb, S. Inorg. Own. Acta 1993, 206, 15. Smith, D. P.; Kohen, E.; Maestre, M. F.; Fish, R. H. Inorg. Chem. 1993, 32, 4119. Smith, D. P.; Griffin, M. T.; Olmstead, M. M ; Maestre, M F.; Fish, R. H. Inorg. Chem. 1993, 32, 4677. (e) Krämer, R.; Polborn, K.; Robl, C.; Beck, W. Inorg. Chim. Acta 1992, 198-200, 415. (f) Ryabov, A. D. Angew. Chem., Int. Ed. Engl. 1991, 30, 931. (g) Kuo, L. Y.; Kanatzidis, M. G.; Sabat, M.; Tipton, A. L.; Marks, T. J. J. Am. Chem. Soc. 1991, 113, 9027.
21. See, e.g.: (a) Jaouen, G.; Vessières, A.; Butler, I. S. Acc. Chem. Res. 1993, 26, 361. (b) Sheldrick, W. S.; Hagen-Eckhard, H. S.; Heeb, S. Inorg. Own. Acta 1993, 206, 15. Smith, D. P.; Kohen, E.; Maestre, M. F.; Fish, R. H. Inorg. Chem. 1993, 32, 4119. Smith, D. P.; Griffin, M. T.; Olmstead, M. M ; Maestre, M F.; Fish, R. H. Inorg. Chem. 1993, 32, 4677. (e) Krämer, R.; Polborn, K.; Robl, C.; Beck, W. Inorg. Chim. Acta 1992, 198-200, 415. (f) Ryabov, A. D. Angew. Chem., Int. Ed. Engl. 1991, 30, 931. (g) Kuo, L. Y.; Kanatzidis, M. G.; Sabat, M.; Tipton, A. L.; Marks, T. J. J. Am. Chem. Soc. 1991, 113, 9027.
22. Arpalahti, J.; Lippert, B.; Schollhorn, H.; Thewalt, U. Inorg. Chim. Acta 1988, 153, 45.
23. -) and filtration of AgCl.
24. Watt, G. W.; Cude, W. A. Inorg. Chem. 1968, 7, 335.
25. Micklitz, W.; Lippert, B.; Schöllhorn, H.; Thewalt, U. J. Heterocycl. Chem. 1989, 26, 1499.
26. Abbreviations used: 1.3-DimeU = free base; 1,3-DimeU-CJ = 1,3-dimethyluracil deprotonated at C5 and metalated at this site; 1-MeUH = free base; 1-MeU-Ay = monoanion, coordinated to metal via N(3); 1-MeU-N3,C5 = dianion, metalated at N(3) and C(5) and possibly a monoanion at low pH (protonated at O(4) or O(2)).
27. (a) Sheldrick, G. M. SHELXTL PLUS (Release 3.4) for Nicolet R3m/V Crystallographic System; University of Göttingen: Gottingen, Germany 1987;
28. (b) Sheldrick, G. M. SHELX-93; University of Göttingen, Göttingen, Germany, 1993.
29. Lippert, B. In ref 1, pp 9-46.
30. Khan, T. B. In ref 1, pp 47-61.
31. (a) Terron, A. Comments Inorg. Chem. 1993, 14, 63.
32. (b) Gellert R. W.; Bau, R. Met. Ions Biol. Syst. 1979, 8, 1.
33. (c) Swaminathan, V.; Sundaralingam, M. CRC Crit. Rev. Biochemistry 1979, 6, 245.
34. Goodgame, M.; Jakubovic, D. A. Coord. Chem. Rev. 1987, 79, 97.
35. Carrabine, J. A.; Sundaralingam, M. Biochemistry 1971, 10, 292.
36. Goodgame, M.; Johns, K. W. J. Chem. Soc., Dalton Trans. 1977, 1680.
37. Goodgame, M.; Johns, K. W. Inorg. Chim. Acta 1978, 30, L 335.
38. Pullman, B.; Pullmann, A. Prog. Nucl. Acid Res. Mol. Biol. 1968, 9, 342.
39. Bradshaw, T. K.; Hutchinson, D. W. Chem. Soc. Rev. 1977, 6, 43.
40. Pregosin, P. S. Annu. Rep. NMR Spectrosc. 1986, 17, 172.
41. Raudaschl, G.; Lippert, B. Inorg. Chim. Acta 1983, 80, L 49 and references cited therein.
42. 2+ ca. 6.3, cf.: (a) Appleton, T. G.; Hall, J. R.; Raiph, S. F.; Thompson, C. S. M. Inorg. Chem. 1989, 28, 1989. (b) Arpalahti, J.; Lehikoinen, P. Inorg. Chem. 1990, 29, 2564.
43. 2+ ca. 6.3, cf.: (a) Appleton, T. G.; Hall, J. R.; Raiph, S. F.; Thompson, C. S. M. Inorg. Chem. 1989, 28, 1989. (b) Arpalahti, J.; Lehikoinen, P. Inorg. Chem. 1990, 29, 2564.
44. See, e.g.: (a) Kosturko, L. D.; Folzer, C.; Stewart, R. F. Biochemistry 1974, 13, 3949. (b) Poojary, M. D.; Manohar, H. Inorg. Chim. Acta 1984, 93, 153 and references cited therein, Menzer, S.; Hillgeris, E. C.; Lippert, B. Inorg. Chim. Acta 1993, 211, 221.
45. See, e.g.: (a) Kosturko, L. D.; Folzer, C.; Stewart, R. F. Biochemistry 1974, 13, 3949. (b) Poojary, M. D.; Manohar, H. Inorg. Chim. Acta 1984, 93, 153 and references cited therein, Menzer, S.; Hillgeris, E. C.; Lippert, B. Inorg. Chim. Acta 1993, 211, 221.
46. See, e.g.: (a) Kosturko, L. D.; Folzer, C.; Stewart, R. F. Biochemistry 1974, 13, 3949. (b) Poojary, M. D.; Manohar, H. Inorg. Chim. Acta 1984, 93, 153 and references cited therein, Menzer, S.; Hillgeris, E. C.; Lippert, B. Inorg. Chim. Acta 1993, 211, 221.
47. Lippert, B.; Neugebauer, D. Inorg. Chim. Acta 1980, 46, 171.
48. Guay, F.; Beauchamp, A. L.; Gilbert, C.; Savoie, R. Can. J. Spectrosc. 1983, 28, 13.
49. (a) Wierzchowski, K. L.; Litonska, E.; Shugar, D. J. Am. Chem. Soc. 1965, 87, 4621.
50. (b) Bandekar, J.; Zundel, G. Spectrochim. Acta 1983, 39 A, 337.
51. Bandekar, J.; Zundel, G. Spectrochim. Acta 1982, 38 A, 815.
52. An authentic sample was prepared and analyzed in analogy to the corresponding 1-methylthymine complex reported by: Kosturko, L. D.; Folzer, C.; Stewart. R. F. Biochemistry 1974, 13, 3949.
53. 2O, pD 5-6).
54. Parshall, G. W. Homogeneous Catalysis; Wiley-Interscience: New York, 1980; Chapter 7.
55. Cordone, R.; Taube, H. J. Am. Chem. Soc. 1987, 109, 8101.
56. Cordone, R.; Harman, W. D.; Taube, H. J. Am. Chem. Soc. 1989, 111, 2896.
57. Frommer, G.; Lianza, F.; Albinati, A.; Lippert, B. Inorg. Chem. 1992, 31, 2434.
58. See, e.g.: (a) Bergstrom, D. E.; Ruth, J. L.; Warwick, P. J. Org. Chem. 1981, 46, 1432. (b) Bergstrom, D.; Beal, P.; Husain, A.; Lind, R.; Jensen, J. J. Am. Chem. Soc. 1989, 111, 374. Peters, D.; Hörnfeldt, A.-B.; Gronowitz, S. J. Heterocycl. Chem. 1991, 28, 1629.
59. See, e.g.: (a) Bergstrom, D. E.; Ruth, J. L.; Warwick, P. J. Org. Chem. 1981, 46, 1432. (b) Bergstrom, D.; Beal, P.; Husain, A.; Lind, R.; Jensen, J. J. Am. Chem. Soc. 1989, 111, 374. Peters, D.; Hörnfeldt, A.-B.; Gronowitz, S. J. Heterocycl. Chem. 1991, 28, 1629.
60. See, e.g.: (a) Bergstrom, D. E.; Ruth, J. L.; Warwick, P. J. Org. Chem. 1981, 46, 1432. (b) Bergstrom, D.; Beal, P.; Husain, A.; Lind, R.; Jensen, J. J. Am. Chem. Soc. 1989, 111, 374. Peters, D.; Hörnfeldt, A.-B.; Gronowitz, S. J. Heterocycl. Chem. 1991, 28, 1629.
61. Robertson, M. P.; Miller, S. L. Science 1995, 268, 702.