Efficient RNA hydrolysis by lanthanide(III)-hydrogen peroxide combinations. Novel aggregates as the catalytic species

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 3, 1998, Pages 523-527

  Kamitani, Jun ^a   Sumaoka, Jun ^a   Asanuma, Hiroyuki ^a   Komiyama, Makoto ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001208219     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a708036k     Document Type: Article

References (57)

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3. Reviews: (a) R. Breslow, Acc. Chem. Res., 1995, 28, 146; (b) E. Kimura and T. Koike, Adv. Inorg. Chem., 1997, 44, 229; (c) M. Komiyama, J. Biochem., 1995, 118, 665; (d) D. M. Perreault and E. V. Anslyn, Angew. Chem., Int. Ed. Engl., 1997, 36, 432.
4. Reviews: (a) R. Breslow, Acc. Chem. Res., 1995, 28, 146; (b) E. Kimura and T. Koike, Adv. Inorg. Chem., 1997, 44, 229; (c) M. Komiyama, J. Biochem., 1995, 118, 665; (d) D. M. Perreault and E. V. Anslyn, Angew. Chem., Int. Ed. Engl., 1997, 36, 432.
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24. Artificial enzymes for sequence-selective RNA scission were prepared by attaching lanthanide complexes to DNA oligomers; (a) K. Matsumura, M. Endo and M. Komiyama, J. Chem. Soc., Chem. Commun., 1994, 2019; (b) D. Magda, R. A. Miller, J. L. Sessler and B. L. Iverson, J. Am. Chem. Soc., 1994, 116, 7439; (c) J. Hall, D. Hüsken and R. Häner, Nucleic Acid Res., 1996, 24, 3522.
25. Artificial enzymes for sequence-selective RNA scission were prepared by attaching lanthanide complexes to DNA oligomers; (a) K. Matsumura, M. Endo and M. Komiyama, J. Chem. Soc., Chem. Commun., 1994, 2019; (b) D. Magda, R. A. Miller, J. L. Sessler and B. L. Iverson, J. Am. Chem. Soc., 1994, 116, 7439; (c) J. Hall, D. Hüsken and R. Häner, Nucleic Acid Res., 1996, 24, 3522.
26. Artificial enzymes for sequence-selective RNA scission were prepared by attaching lanthanide complexes to DNA oligomers; (a) K. Matsumura, M. Endo and M. Komiyama, J. Chem. Soc., Chem. Commun., 1994, 2019; (b) D. Magda, R. A. Miller, J. L. Sessler and B. L. Iverson, J. Am. Chem. Soc., 1994, 116, 7439; (c) J. Hall, D. Hüsken and R. Häner, Nucleic Acid Res., 1996, 24, 3522.
27. Non-enzymatic hydrolysis of DNA was also achieved by lanthanide ions: (a) Y. Matsumoto and M. Komiyama, Nucleic Acids Symp. Ser., 1992, 27, 33; (b) M. Komiyama, K. Matsumura, K. Yonezawa and Y. Matsumoto, Chem. Express, 1993, 8, 85; (c) T. Shiiba, K. Yonezawa N. Takeda, Y. Matsumoto, M. Yashiro and M. Komiyama, J. Mol. Catal., 1993, 84, L21; (d) B. K. Takasaki and J. Chin, J. Am. Chem. Soc., 1994, 116, 1121; (e) M. Komiyama, T. Shiiba, T. Kodama, N. Takeda, J. Sumaoka and M. Yashiro, Chem. Lett., 1994, 1025; (f) M. Komiyama, N. Takeda, Y. Takahashi, H. Uchida, T. Shiiba, T. Kodama and M. Yashiro, J. Chem. Soc., Perkin Trans. 2, 1995, 269; (g) J. Rammo, R. Hettich, A. Roigk and H.-J. Schneider, J. Chem. Soc., Chem. Commun., 1996, 105; (h) S. Hashimoto and Y. Nakamura, J. Chem. Soc., Perkin Trans. 1, 1996, 2623.
28. Non-enzymatic hydrolysis of DNA was also achieved by lanthanide ions: (a) Y. Matsumoto and M. Komiyama, Nucleic Acids Symp. Ser., 1992, 27, 33; (b) M. Komiyama, K. Matsumura, K. Yonezawa and Y. Matsumoto, Chem. Express, 1993, 8, 85; (c) T. Shiiba, K. Yonezawa N. Takeda, Y. Matsumoto, M. Yashiro and M. Komiyama, J. Mol. Catal., 1993, 84, L21; (d) B. K. Takasaki and J. Chin, J. Am. Chem. Soc., 1994, 116, 1121; (e) M. Komiyama, T. Shiiba, T. Kodama, N. Takeda, J. Sumaoka and M. Yashiro, Chem. Lett., 1994, 1025; (f) M. Komiyama, N. Takeda, Y. Takahashi, H. Uchida, T. Shiiba, T. Kodama and M. Yashiro, J. Chem. Soc., Perkin Trans. 2, 1995, 269; (g) J. Rammo, R. Hettich, A. Roigk and H.-J. Schneider, J. Chem. Soc., Chem. Commun., 1996, 105; (h) S. Hashimoto and Y. Nakamura, J. Chem. Soc., Perkin Trans. 1, 1996, 2623.
29. Non-enzymatic hydrolysis of DNA was also achieved by lanthanide ions: (a) Y. Matsumoto and M. Komiyama, Nucleic Acids Symp. Ser., 1992, 27, 33; (b) M. Komiyama, K. Matsumura, K. Yonezawa and Y. Matsumoto, Chem. Express, 1993, 8, 85; (c) T. Shiiba, K. Yonezawa N. Takeda, Y. Matsumoto, M. Yashiro and M. Komiyama, J. Mol. Catal., 1993, 84, L21; (d) B. K. Takasaki and J. Chin, J. Am. Chem. Soc., 1994, 116, 1121; (e) M. Komiyama, T. Shiiba, T. Kodama, N. Takeda, J. Sumaoka and M. Yashiro, Chem. Lett., 1994, 1025; (f) M. Komiyama, N. Takeda, Y. Takahashi, H. Uchida, T. Shiiba, T. Kodama and M. Yashiro, J. Chem. Soc., Perkin Trans. 2, 1995, 269; (g) J. Rammo, R. Hettich, A. Roigk and H.-J. Schneider, J. Chem. Soc., Chem. Commun., 1996, 105; (h) S. Hashimoto and Y. Nakamura, J. Chem. Soc., Perkin Trans. 1, 1996, 2623.
30. Non-enzymatic hydrolysis of DNA was also achieved by lanthanide ions: (a) Y. Matsumoto and M. Komiyama, Nucleic Acids Symp. Ser., 1992, 27, 33; (b) M. Komiyama, K. Matsumura, K. Yonezawa and Y. Matsumoto, Chem. Express, 1993, 8, 85; (c) T. Shiiba, K. Yonezawa N. Takeda, Y. Matsumoto, M. Yashiro and M. Komiyama, J. Mol. Catal., 1993, 84, L21; (d) B. K. Takasaki and J. Chin, J. Am. Chem. Soc., 1994, 116, 1121; (e) M. Komiyama, T. Shiiba, T. Kodama, N. Takeda, J. Sumaoka and M. Yashiro, Chem. Lett., 1994, 1025; (f) M. Komiyama, N. Takeda, Y. Takahashi, H. Uchida, T. Shiiba, T. Kodama and M. Yashiro, J. Chem. Soc., Perkin Trans. 2, 1995, 269; (g) J. Rammo, R. Hettich, A. Roigk and H.-J. Schneider, J. Chem. Soc., Chem. Commun., 1996, 105; (h) S. Hashimoto and Y. Nakamura, J. Chem. Soc., Perkin Trans. 1, 1996, 2623.
31. Non-enzymatic hydrolysis of DNA was also achieved by lanthanide ions: (a) Y. Matsumoto and M. Komiyama, Nucleic Acids Symp. Ser., 1992, 27, 33; (b) M. Komiyama, K. Matsumura, K. Yonezawa and Y. Matsumoto, Chem. Express, 1993, 8, 85; (c) T. Shiiba, K. Yonezawa N. Takeda, Y. Matsumoto, M. Yashiro and M. Komiyama, J. Mol. Catal., 1993, 84, L21; (d) B. K. Takasaki and J. Chin, J. Am. Chem. Soc., 1994, 116, 1121; (e) M. Komiyama, T. Shiiba, T. Kodama, N. Takeda, J. Sumaoka and M. Yashiro, Chem. Lett., 1994, 1025; (f) M. Komiyama, N. Takeda, Y. Takahashi, H. Uchida, T. Shiiba, T. Kodama and M. Yashiro, J. Chem. Soc., Perkin Trans. 2, 1995, 269; (g) J. Rammo, R. Hettich, A. Roigk and H.-J. Schneider, J. Chem. Soc., Chem. Commun., 1996, 105; (h) S. Hashimoto and Y. Nakamura, J. Chem. Soc., Perkin Trans. 1, 1996, 2623.
32. Non-enzymatic hydrolysis of DNA was also achieved by lanthanide ions: (a) Y. Matsumoto and M. Komiyama, Nucleic Acids Symp. Ser., 1992, 27, 33; (b) M. Komiyama, K. Matsumura, K. Yonezawa and Y. Matsumoto, Chem. Express, 1993, 8, 85; (c) T. Shiiba, K. Yonezawa N. Takeda, Y. Matsumoto, M. Yashiro and M. Komiyama, J. Mol. Catal., 1993, 84, L21; (d) B. K. Takasaki and J. Chin, J. Am. Chem. Soc., 1994, 116, 1121; (e) M. Komiyama, T. Shiiba, T. Kodama, N. Takeda, J. Sumaoka and M. Yashiro, Chem. Lett., 1994, 1025; (f) M. Komiyama, N. Takeda, Y. Takahashi, H. Uchida, T. Shiiba, T. Kodama and M. Yashiro, J. Chem. Soc., Perkin Trans. 2, 1995, 269; (g) J. Rammo, R. Hettich, A. Roigk and H.-J. Schneider, J. Chem. Soc., Chem. Commun., 1996, 105; (h) S. Hashimoto and Y. Nakamura, J. Chem. Soc., Perkin Trans. 1, 1996, 2623.
33. Non-enzymatic hydrolysis of DNA was also achieved by lanthanide ions: (a) Y. Matsumoto and M. Komiyama, Nucleic Acids Symp. Ser., 1992, 27, 33; (b) M. Komiyama, K. Matsumura, K. Yonezawa and Y. Matsumoto, Chem. Express, 1993, 8, 85; (c) T. Shiiba, K. Yonezawa N. Takeda, Y. Matsumoto, M. Yashiro and M. Komiyama, J. Mol. Catal., 1993, 84, L21; (d) B. K. Takasaki and J. Chin, J. Am. Chem. Soc., 1994, 116, 1121; (e) M. Komiyama, T. Shiiba, T. Kodama, N. Takeda, J. Sumaoka and M. Yashiro, Chem. Lett., 1994, 1025; (f) M. Komiyama, N. Takeda, Y. Takahashi, H. Uchida, T. Shiiba, T. Kodama and M. Yashiro, J. Chem. Soc., Perkin Trans. 2, 1995, 269; (g) J. Rammo, R. Hettich, A. Roigk and H.-J. Schneider, J. Chem. Soc., Chem. Commun., 1996, 105; (h) S. Hashimoto and Y. Nakamura, J. Chem. Soc., Perkin Trans. 1, 1996, 2623.
34. Non-enzymatic hydrolysis of DNA was also achieved by lanthanide ions: (a) Y. Matsumoto and M. Komiyama, Nucleic Acids Symp. Ser., 1992, 27, 33; (b) M. Komiyama, K. Matsumura, K. Yonezawa and Y. Matsumoto, Chem. Express, 1993, 8, 85; (c) T. Shiiba, K. Yonezawa N. Takeda, Y. Matsumoto, M. Yashiro and M. Komiyama, J. Mol. Catal., 1993, 84, L21; (d) B. K. Takasaki and J. Chin, J. Am. Chem. Soc., 1994, 116, 1121; (e) M. Komiyama, T. Shiiba, T. Kodama, N. Takeda, J. Sumaoka and M. Yashiro, Chem. Lett., 1994, 1025; (f) M. Komiyama, N. Takeda, Y. Takahashi, H. Uchida, T. Shiiba, T. Kodama and M. Yashiro, J. Chem. Soc., Perkin Trans. 2, 1995, 269; (g) J. Rammo, R. Hettich, A. Roigk and H.-J. Schneider, J. Chem. Soc., Chem. Commun., 1996, 105; (h) S. Hashimoto and Y. Nakamura, J. Chem. Soc., Perkin Trans. 1, 1996, 2623.
35. Hydrolysis of other phosphodiesters: (a) K. Matsumura and M. Komiyama, J. Inorg. Biochem., 1994, 55, 153; (b) Ref. 2.
36. Phosphotriester hydrolysis: R. W. Hay and N. Govan, J. Chem. Soc., Chem. Commun., 1990, 714.
37. B. K. Takasaki and J. Chin, J. Am. Chem. Soc., 1993, 115, 9337; 1995, 117, 8582.
38. B. K. Takasaki and J. Chin, J. Am. Chem. Soc., 1993, 115, 9337; 1995, 117, 8582.
39. 2 combination was used as the catalytic site in an enyme model: R. Breslow and B. Zhang, J. Am. Chem. Soc., 1994, 116, 7893.
40. III complex is unstable and loses activity after about 30 min'. In our experiments, however, no significant deterioration of the catalyst was observed even after 100 min of pre-incubation. As noted in the Experimental section, fairly good pseudo-first-order kinetics was obtained. The reason for the discrepancy is not clear.
41. -1.
42. III concentrations (0.1-4 mM), and obtained a similar result to Takasaki and Chin. Therefore, notable differences in the kinetic features between RNA hydrolysis and BNPP hydrolysis really come from the differences in the leaving group of substrates, and not simply from the differences in the reaction conditions employed.
43. 0 ratio of 0.05. Thus, all the protons are from hydrogen peroxide, and not from water molecules.
44. -23 M).
45. 2 are sufficiently great. The experimental points in Fig. 4 are far from the theoretical line (the broken one), which was calculated by using the parameters reported by Takasaki and Chin.
46. 0 causes only a small increase in the concentration of the dinuclear complex.
47. 3], might be making some contributions in the catalysis.
48. M. L. Bender, R. J. Bergeron and M. Komiyama, The Bioorganic Chemistry of Enzymatic Catalysis, Wiley-Interscience, New York, 1984, p. 133.
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