Catalytic hydrolysis of phosphate diesters by Lanthanide(III) Cryptate (2.2.1) complexes

Inorganic Chemistry

Volumn 35, Issue 13, 1996, Pages 3780-3785

  Oh, Soon Jin ^a   Song, Kyong Hwa ^a   Whang, Dongmok ^a   Kim, Kimoon ^a   Yoon, Tae Hyun ^a,b   Moon, Hichung ^a,b   Park, Joon Won ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

^b Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001351979     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic9510526     Document Type: Article

References (52)

1. (a) Bashkin, J. K.; Jenkins, L. A. Comments Inorg. Chem. 1994, 16, 77-93.
2. (b) Sigman, D. A.; Bruice, T. W.; Mazumder, A.; Sutton, C L Acc. Chem. Res. 1993, 26, 98-104.
3. (c) Chin, J. Acc. Chem. Res. 1991, 24, 145-152.
4. (d) Hendry, P.; Sargeson, A. M. In Progress in inorganic Chemistry; Lippard, S. J , Ed.; John Wiley & Sons: New York, 1990; Vol. 38, pp 201-258.
5. (e) Uhlenbeck, O. C. Nature 1987, 328, 596-600.
6. (f) Westheimer, F. H. Science 1987, 235, 1173-1178.
7. (g) Sigman, D. S. Acc. Chem. Res 1986, 19, 180-186.
8. (h) Westheimer, F. H. Pure Appl. Chem. 1977, 49, 1059-1067.
9. The catalytic hydrolysis of RNA is under active research. For these activities, see: (a) Linkletter, B.; Chin, J. Angew. Chem. Int. Ed. Engl. 1995, 34, 472-474. (b) Amin, S.; Morrow, J. R., Lake, C. H.; Churchill, M. R. Angew. Chem. Int. Ed. Engl. 1994, 33, 773-775. (c) Hayashi, N.; Takeda, N.; Shiiba, T.; Yashiro, M.; Watanabe, K.; Komiyama, M. Inorg. Chem 1993, 32, 5899-5900. (d) Kolasa, K. A.. Morrow, J. R.; Sharma, A. P. Inorg. Chem. 1993, 32, 3983-3984. (e) Morrow, J. R.; Buttrey, L. A.; Shelton, V. M.; Berback, K. A. J. Am. Chem. Soc. 1992, 114, 1903-1905 (f) Modak, A. S.; Gard, J. K.; Merriman, M. C.; Winkeler, K. A., Bashkin, J. K.; Stern, M. K. J. Am. Chem. Soc. 1991, 113, 283-29. (g) Yoshinari, K.; Yamazaki, K.; Komiyama, M. J. Am. Chem. Soc. 1991, 113, 5899-5901. (h) Stern, M. K.; Bashkin, J. K.; Sall, E. D. J. Am. Chem. Soc 1990, 112, 5357-5359.
10. The catalytic hydrolysis of RNA is under active research. For these activities, see: (a) Linkletter, B.; Chin, J. Angew. Chem. Int. Ed. Engl. 1995, 34, 472-474. (b) Amin, S.; Morrow, J. R., Lake, C. H.; Churchill, M. R. Angew. Chem. Int. Ed. Engl. 1994, 33, 773-775. (c) Hayashi, N.; Takeda, N.; Shiiba, T.; Yashiro, M.; Watanabe, K.; Komiyama, M. Inorg. Chem 1993, 32, 5899-5900. (d) Kolasa, K. A.. Morrow, J. R.; Sharma, A. P. Inorg. Chem. 1993, 32, 3983-3984. (e) Morrow, J. R.; Buttrey, L. A.; Shelton, V. M.; Berback, K. A. J. Am. Chem. Soc. 1992, 114, 1903-1905 (f) Modak, A. S.; Gard, J. K.; Merriman, M. C.; Winkeler, K. A., Bashkin, J. K.; Stern, M. K. J. Am. Chem. Soc. 1991, 113, 283-29. (g) Yoshinari, K.; Yamazaki, K.; Komiyama, M. J. Am. Chem. Soc. 1991, 113, 5899-5901. (h) Stern, M. K.; Bashkin, J. K.; Sall, E. D. J. Am. Chem. Soc 1990, 112, 5357-5359.
11. The catalytic hydrolysis of RNA is under active research. For these activities, see: (a) Linkletter, B.; Chin, J. Angew. Chem. Int. Ed. Engl. 1995, 34, 472-474. (b) Amin, S.; Morrow, J. R., Lake, C. H.; Churchill, M. R. Angew. Chem. Int. Ed. Engl. 1994, 33, 773-775. (c) Hayashi, N.; Takeda, N.; Shiiba, T.; Yashiro, M.; Watanabe, K.; Komiyama, M. Inorg. Chem 1993, 32, 5899-5900. (d) Kolasa, K. A.. Morrow, J. R.; Sharma, A. P. Inorg. Chem. 1993, 32, 3983-3984. (e) Morrow, J. R.; Buttrey, L. A.; Shelton, V. M.; Berback, K. A. J. Am. Chem. Soc. 1992, 114, 1903-1905 (f) Modak, A. S.; Gard, J. K.; Merriman, M. C.; Winkeler, K. A., Bashkin, J. K.; Stern, M. K. J. Am. Chem. Soc. 1991, 113, 283-29. (g) Yoshinari, K.; Yamazaki, K.; Komiyama, M. J. Am. Chem. Soc. 1991, 113, 5899-5901. (h) Stern, M. K.; Bashkin, J. K.; Sall, E. D. J. Am. Chem. Soc 1990, 112, 5357-5359.
12. The catalytic hydrolysis of RNA is under active research. For these activities, see: (a) Linkletter, B.; Chin, J. Angew. Chem. Int. Ed. Engl. 1995, 34, 472-474. (b) Amin, S.; Morrow, J. R., Lake, C. H.; Churchill, M. R. Angew. Chem. Int. Ed. Engl. 1994, 33, 773-775. (c) Hayashi, N.; Takeda, N.; Shiiba, T.; Yashiro, M.; Watanabe, K.; Komiyama, M. Inorg. Chem 1993, 32, 5899-5900. (d) Kolasa, K. A.. Morrow, J. R.; Sharma, A. P. Inorg. Chem. 1993, 32, 3983-3984. (e) Morrow, J. R.; Buttrey, L. A.; Shelton, V. M.; Berback, K. A. J. Am. Chem. Soc. 1992, 114, 1903-1905 (f) Modak, A. S.; Gard, J. K.; Merriman, M. C.; Winkeler, K. A., Bashkin, J. K.; Stern, M. K. J. Am. Chem. Soc. 1991, 113, 283-29. (g) Yoshinari, K.; Yamazaki, K.; Komiyama, M. J. Am. Chem. Soc. 1991, 113, 5899-5901. (h) Stern, M. K.; Bashkin, J. K.; Sall, E. D. J. Am. Chem. Soc 1990, 112, 5357-5359.
13. The catalytic hydrolysis of RNA is under active research. For these activities, see: (a) Linkletter, B.; Chin, J. Angew. Chem. Int. Ed. Engl. 1995, 34, 472-474. (b) Amin, S.; Morrow, J. R., Lake, C. H.; Churchill, M. R. Angew. Chem. Int. Ed. Engl. 1994, 33, 773-775. (c) Hayashi, N.; Takeda, N.; Shiiba, T.; Yashiro, M.; Watanabe, K.; Komiyama, M. Inorg. Chem 1993, 32, 5899-5900. (d) Kolasa, K. A.. Morrow, J. R.; Sharma, A. P. Inorg. Chem. 1993, 32, 3983-3984. (e) Morrow, J. R.; Buttrey, L. A.; Shelton, V. M.; Berback, K. A. J. Am. Chem. Soc. 1992, 114, 1903-1905 (f) Modak, A. S.; Gard, J. K.; Merriman, M. C.; Winkeler, K. A., Bashkin, J. K.; Stern, M. K. J. Am. Chem. Soc. 1991, 113, 283-29. (g) Yoshinari, K.; Yamazaki, K.; Komiyama, M. J. Am. Chem. Soc. 1991, 113, 5899-5901. (h) Stern, M. K.; Bashkin, J. K.; Sall, E. D. J. Am. Chem. Soc 1990, 112, 5357-5359.
14. The catalytic hydrolysis of RNA is under active research. For these activities, see: (a) Linkletter, B.; Chin, J. Angew. Chem. Int. Ed. Engl. 1995, 34, 472-474. (b) Amin, S.; Morrow, J. R., Lake, C. H.; Churchill, M. R. Angew. Chem. Int. Ed. Engl. 1994, 33, 773-775. (c) Hayashi, N.; Takeda, N.; Shiiba, T.; Yashiro, M.; Watanabe, K.; Komiyama, M. Inorg. Chem 1993, 32, 5899-5900. (d) Kolasa, K. A.. Morrow, J. R.; Sharma, A. P. Inorg. Chem. 1993, 32, 3983-3984. (e) Morrow, J. R.; Buttrey, L. A.; Shelton, V. M.; Berback, K. A. J. Am. Chem. Soc. 1992, 114, 1903-1905 (f) Modak, A. S.; Gard, J. K.; Merriman, M. C.; Winkeler, K. A., Bashkin, J. K.; Stern, M. K. J. Am. Chem. Soc. 1991, 113, 283-29. (g) Yoshinari, K.; Yamazaki, K.; Komiyama, M. J. Am. Chem. Soc. 1991, 113, 5899-5901. (h) Stern, M. K.; Bashkin, J. K.; Sall, E. D. J. Am. Chem. Soc 1990, 112, 5357-5359.
15. The catalytic hydrolysis of RNA is under active research. For these activities, see: (a) Linkletter, B.; Chin, J. Angew. Chem. Int. Ed. Engl. 1995, 34, 472-474. (b) Amin, S.; Morrow, J. R., Lake, C. H.; Churchill, M. R. Angew. Chem. Int. Ed. Engl. 1994, 33, 773-775. (c) Hayashi, N.; Takeda, N.; Shiiba, T.; Yashiro, M.; Watanabe, K.; Komiyama, M. Inorg. Chem 1993, 32, 5899-5900. (d) Kolasa, K. A.. Morrow, J. R.; Sharma, A. P. Inorg. Chem. 1993, 32, 3983-3984. (e) Morrow, J. R.; Buttrey, L. A.; Shelton, V. M.; Berback, K. A. J. Am. Chem. Soc. 1992, 114, 1903-1905 (f) Modak, A. S.; Gard, J. K.; Merriman, M. C.; Winkeler, K. A., Bashkin, J. K.; Stern, M. K. J. Am. Chem. Soc. 1991, 113, 283-29. (g) Yoshinari, K.; Yamazaki, K.; Komiyama, M. J. Am. Chem. Soc. 1991, 113, 5899-5901. (h) Stern, M. K.; Bashkin, J. K.; Sall, E. D. J. Am. Chem. Soc 1990, 112, 5357-5359.
16. The catalytic hydrolysis of RNA is under active research. For these activities, see: (a) Linkletter, B.; Chin, J. Angew. Chem. Int. Ed. Engl. 1995, 34, 472-474. (b) Amin, S.; Morrow, J. R., Lake, C. H.; Churchill, M. R. Angew. Chem. Int. Ed. Engl. 1994, 33, 773-775. (c) Hayashi, N.; Takeda, N.; Shiiba, T.; Yashiro, M.; Watanabe, K.; Komiyama, M. Inorg. Chem 1993, 32, 5899-5900. (d) Kolasa, K. A.. Morrow, J. R.; Sharma, A. P. Inorg. Chem. 1993, 32, 3983-3984. (e) Morrow, J. R.; Buttrey, L. A.; Shelton, V. M.; Berback, K. A. J. Am. Chem. Soc. 1992, 114, 1903-1905 (f) Modak, A. S.; Gard, J. K.; Merriman, M. C.; Winkeler, K. A., Bashkin, J. K.; Stern, M. K. J. Am. Chem. Soc. 1991, 113, 283-29. (g) Yoshinari, K.; Yamazaki, K.; Komiyama, M. J. Am. Chem. Soc. 1991, 113, 5899-5901. (h) Stern, M. K.; Bashkin, J. K.; Sall, E. D. J. Am. Chem. Soc 1990, 112, 5357-5359.
17. (a) Kim, N.; Suh, J. J. Org. Chem. 1994, 59, 1561-1571.
18. (b) Weijnen, J. G J.; Engbersen, J. F. J. Recl. Trav. Chim. Pays-Bas 1993, 112 351-357.
19. (c) Browne, K. A.; Bruice, T. C. J. Am. Chem. Soc. 1992, 114, 4951-4958.
20. (d) De Rosch, M. A., Trogler, W. C. Inorg. Chem. 1990, 29, 2409-2416.
21. (a) Kim J. H.; Chin, J. J. Am. Chem. Soc. 1992, 114, 9792-9795.
22. (b) Chung, Y.; Akkaya, E. U.; Venkatachalam, T. K.; Czarnik, A W. Tetrahedron Lett. 1990, 31, 5413-5416.
23. (c) Chin, J.; Banaszczyk, M.; Jubian, V.; Zou, X. J. Am. Chem. Soc. 1989, 111, 186-190.
24. (d) Chin, J.; Zou, X. J. J. Am. Chem. Soc. 1988, 110, 223-225.
25. (e) Rawji, G. H.; Milburn, R. M. Inorg. Chim. Acta 1988, 150, 227-232
26. (a) Wall, M.; Resemary, C. H.; Chin, J. Angew. Chem. Int. Ed. Engl 1993, 32, 1633-1635.
27. (b) Morrow, J.; Trogler, W. C. Inorg. Chem. 1988, 27, 3387-3394.
28. (a) Shionoya, M.; Kimura, E.; Shiro, M. J. Am. Chem. Soc. 1993, 115, 6730-6737.
29. (b) Koike, T.; Kimura, E.; Nakamura, I.; Hashimoto, Y.; Shiro, M. J. Am. Chem. Soc. 1992, 114, 7338-7345.
30. (c) Koike, T.; Kimura, E. J. Am. Chem. Soc. 1991, 113, 8935-8941.
31. Hendry, P.; Sargeson, A. M. J. Am. Chem. Soc. 1989, 111, 2521-2527.
32. Breslow, R.; Huang, D.-L. Proc. Natl. Acad. Sci. U.S.A. 1991, 88 4080-4083.
33. (a) Takasaki, B. K.; Chin, J. J. Am. Chem. Soc. 1994, 116, 1121-1122.
34. (b) Sumaoka, J ; Miyama, S., Komiyama, M. J. Chem. Soc., Chem. Commun. 1994, 1755-1756.
35. (c) Breslow, R.; Zhang, B. J. Am. Chem. Soc. 1994, 116, 7893-7894.
36. (d) Amin, S.; Morrow, J. R., Lake, C. H.; Churchill, M. R. Angew. Chem., Int. Ed. Engl. 1994, 33, 773-775.
37. (e) Schneider, H.-J.; Rammo, J.; Hettich, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1716-1719.
38. (f) Takasaki, B. K.; Chin, J. J. Am. Chem. Soc. 1993, 115, 9337-9338.
39. (a) Magda, D.; Miller, K. A.; Sessler, J. L.; Iverson, B L. J. Am. Chem. Soc. 1994, 116, 7439-7440.
40. (b) Matsumura, K ; Endo, M.; Komiyama, M. J. Chem Soc., Chem. Commun. 1994, 2019-2020.
41. 12 For general information on lanthanide macrocyclic complexes, see: (a) Adachi, G. Y.; Hirashima, Y. In Cation Binding by Macrocodes: Inoue, Y., Gokel, G. W., Eds.; Marcel Dekker: New York, 1990: pp 701-741. (b) Bunzli, J.-C; Wessner, D. Coord. Chem. Rev. 1984, 60, 191-253.
42. 12 For general information on lanthanide macrocyclic complexes, see: (a) Adachi, G. Y.; Hirashima, Y. In Cation Binding by Macrocodes: Inoue, Y., Gokel, G. W., Eds.; Marcel Dekker: New York, 1990: pp 701-741. (b) Bunzli, J.-C; Wessner, D. Coord. Chem. Rev. 1984, 60, 191-253.
43. (a) Oh, S. J.; Song, K. H.; Park, J. W. J. Chem. Soc., Chem. Commun. 1995, 575-576.
44. (b) Oh, S. J.; Yoon, C. W.; Park, J. W. J. Chem. Soc., Perkin Trans. 2 1996, 329-331.
45. Almasio, M.-C.; Arnaud-Neu, F.; Schwing-Weill, M.-J. Helv. Chim. Acta 1983, 66, 1296-1306.
46. Yoon, T. H.; Moon, H.; Park, Y. J., Park, K. K. Environ. Sci Technol. 1994, 28, 2139-2146.
47. From the control experiments, the free lanthanide ions show comparable reactivity, but the reactivity is reduced significantly by addition of sodium acetate at the controlled pH.
48. Moore, J. W.; Pearson, R. G. Kinetics and Mechanism; John Wiley & Sons: New York, 1981; pp 290-296.
49. -1 at pH of 7.0 and 50 °C. See reference 4d.
50. The crystal structure of Eu(2.2.2.) perchlorate shows that a perchlorate anion acting as a bidentate ligand binds to the metal center. Also it is easily seen that the Eu(2.2.1) complex provides wider open space for incoming substrates. For the crystal structure of Eu(2.2.2) perchlorate, see: Ciampolini, M.; Dapporto, P.; Nardi, N. J. Chem. Soc. Dalton 1979, 974.
51. Horrocks, W. D., Sudnick, D. R. J. Am. Chem. Soc 1979, 101, 334-340.
52. For full spectroscopic properties of the complex 1c. see. Sabbatini, N.; Dellonte, S.; Ciano, M.; Bonazzi, A.; Balzani, V. Chem. Phys. Lett. 1984, 107, 212-216.