Rapid and highly selective cleavage of ribonucleoside 2′,3′-cyclic monophosphates by dinuclear CuII complexes

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 23, 1997, Pages 2678-2680

  Liu, Shanghao ^a   Luo, Zhiyong ^a   Hamilton, Andrew D ^a,b  

^a UNIVERSITY OF PITTSBURGH   (United States)

^b YALE UNIVERSITY   (United States)

Author keywords

Enzyme mimetics; Hydrolyses; RNA

Indexed keywords

EID: 0031573890     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199726781     Document Type: Article

References (45)

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2. Reviews : a) M. Komiyama, J. Biochem. 1995, 118, 665; b) J. R. Morrow, Adv. Inorg. Biochem. 1994, 9, 41; c) M. W. Gobel, Angew. Chem. 1994, 106, 1201; Angew. Chem. Int. Ed. Engl. 1994, 33, 1141; d) D. S. Sigman, A. Mazumder, D. M. Perrin, Chem. Rev. 1993, 93, 2295; e) J. Chin, Acc. Chem. Res. 1991, 24, 145.
3. Reviews : a) M. Komiyama, J. Biochem. 1995, 118, 665; b) J. R. Morrow, Adv. Inorg. Biochem. 1994, 9, 41; c) M. W. Gobel, Angew. Chem. 1994, 106, 1201; Angew. Chem. Int. Ed. Engl. 1994, 33, 1141; d) D. S. Sigman, A. Mazumder, D. M. Perrin, Chem. Rev. 1993, 93, 2295; e) J. Chin, Acc. Chem. Res. 1991, 24, 145.
4. Reviews : a) M. Komiyama, J. Biochem. 1995, 118, 665; b) J. R. Morrow, Adv. Inorg. Biochem. 1994, 9, 41; c) M. W. Gobel, Angew. Chem. 1994, 106, 1201; Angew. Chem. Int. Ed. Engl. 1994, 33, 1141; d) D. S. Sigman, A. Mazumder, D. M. Perrin, Chem. Rev. 1993, 93, 2295; e) J. Chin, Acc. Chem. Res. 1991, 24, 145.
5. Reviews : a) M. Komiyama, J. Biochem. 1995, 118, 665; b) J. R. Morrow, Adv. Inorg. Biochem. 1994, 9, 41; c) M. W. Gobel, Angew. Chem. 1994, 106, 1201; Angew. Chem. Int. Ed. Engl. 1994, 33, 1141; d) D. S. Sigman, A. Mazumder, D. M. Perrin, Chem. Rev. 1993, 93, 2295; e) J. Chin, Acc. Chem. Res. 1991, 24, 145.
6. Reviews : a) M. Komiyama, J. Biochem. 1995, 118, 665; b) J. R. Morrow, Adv. Inorg. Biochem. 1994, 9, 41; c) M. W. Gobel, Angew. Chem. 1994, 106, 1201; Angew. Chem. Int. Ed. Engl. 1994, 33, 1141; d) D. S. Sigman, A. Mazumder, D. M. Perrin, Chem. Rev. 1993, 93, 2295; e) J. Chin, Acc. Chem. Res. 1991, 24, 145.
7. Recent examples: a) P.Hurst, B. K.Takasaki, J. Chin, J. Am. Chem. Soc. 1996, 118, 9982; b) M.J. Young, J. Chin, ibid. 1995, 117, 10577; c) B. Linkletter, J. Chin, Angew. Chem. 1995, 107; 529; Angew. Chem. Int. Ed. Engl. 1995, 34, 472; d) W. H. Chapman, Jr., R. Breslow, J. Am. Chem. Soc. 1995, 117, 5462; e) M. Yashiro, A. Ishikubu, M. Komoyama, J. Chem. Soc. Chem. Commun. 1997, 83; f) M. Yashiro, A. Ishikubu, M. Komiyama, ibid. 1995, 1793; g) M. Komiyama, N. Takeda, M. Irisawa, M. Yashiro in DNA and RNA Cleavers and Chemotherapy of Cancer and Viral Diseases (Ed.: B. Meunier), Kluwer, Boston, 1996, p. 321; h) J. K. Bashkin, J. Xie, A.T. Daniher, L. A. Jenkins, G. C. Yeh, ibid. p. 355-366; i) R. Haner, J. Hall, D. Husken, H. E. Moser, ibid. p. 307; j) D. Magda, R. A. Miller, M. Wright, J. Rao, ibid. p. 337.
8. Recent examples: a) P.Hurst, B. K.Takasaki, J. Chin, J. Am. Chem. Soc. 1996, 118, 9982; b) M.J. Young, J. Chin, ibid. 1995, 117, 10577; c) B. Linkletter, J. Chin, Angew. Chem. 1995, 107; 529; Angew. Chem. Int. Ed. Engl. 1995, 34, 472; d) W. H. Chapman, Jr., R. Breslow, J. Am. Chem. Soc. 1995, 117, 5462; e) M. Yashiro, A. Ishikubu, M. Komoyama, J. Chem. Soc. Chem. Commun. 1997, 83; f) M. Yashiro, A. Ishikubu, M. Komiyama, ibid. 1995, 1793; g) M. Komiyama, N. Takeda, M. Irisawa, M. Yashiro in DNA and RNA Cleavers and Chemotherapy of Cancer and Viral Diseases (Ed.: B. Meunier), Kluwer, Boston, 1996, p. 321; h) J. K. Bashkin, J. Xie, A.T. Daniher, L. A. Jenkins, G. C. Yeh, ibid. p. 355-366; i) R. Haner, J. Hall, D. Husken, H. E. Moser, ibid. p. 307; j) D. Magda, R. A. Miller, M. Wright, J. Rao, ibid. p. 337.
9. Recent examples: a) P.Hurst, B. K.Takasaki, J. Chin, J. Am. Chem. Soc. 1996, 118, 9982; b) M.J. Young, J. Chin, ibid. 1995, 117, 10577; c) B. Linkletter, J. Chin, Angew. Chem. 1995, 107; 529; Angew. Chem. Int. Ed. Engl. 1995, 34, 472; d) W. H. Chapman, Jr., R. Breslow, J. Am. Chem. Soc. 1995, 117, 5462; e) M. Yashiro, A. Ishikubu, M. Komoyama, J. Chem. Soc. Chem. Commun. 1997, 83; f) M. Yashiro, A. Ishikubu, M. Komiyama, ibid. 1995, 1793; g) M. Komiyama, N. Takeda, M. Irisawa, M. Yashiro in DNA and RNA Cleavers and Chemotherapy of Cancer and Viral Diseases (Ed.: B. Meunier), Kluwer, Boston, 1996, p. 321; h) J. K. Bashkin, J. Xie, A.T. Daniher, L. A. Jenkins, G. C. Yeh, ibid. p. 355-366; i) R. Haner, J. Hall, D. Husken, H. E. Moser, ibid. p. 307; j) D. Magda, R. A. Miller, M. Wright, J. Rao, ibid. p. 337.
10. Recent examples: a) P.Hurst, B. K.Takasaki, J. Chin, J. Am. Chem. Soc. 1996, 118, 9982; b) M.J. Young, J. Chin, ibid. 1995, 117, 10577; c) B. Linkletter, J. Chin, Angew. Chem. 1995, 107; 529; Angew. Chem. Int. Ed. Engl. 1995, 34, 472; d) W. H. Chapman, Jr., R. Breslow, J. Am. Chem. Soc. 1995, 117, 5462; e) M. Yashiro, A. Ishikubu, M. Komoyama, J. Chem. Soc. Chem. Commun. 1997, 83; f) M. Yashiro, A. Ishikubu, M. Komiyama, ibid. 1995, 1793; g) M. Komiyama, N. Takeda, M. Irisawa, M. Yashiro in DNA and RNA Cleavers and Chemotherapy of Cancer and Viral Diseases (Ed.: B. Meunier), Kluwer, Boston, 1996, p. 321; h) J. K. Bashkin, J. Xie, A.T. Daniher, L. A. Jenkins, G. C. Yeh, ibid. p. 355-366; i) R. Haner, J. Hall, D. Husken, H. E. Moser, ibid. p. 307; j) D. Magda, R. A. Miller, M. Wright, J. Rao, ibid. p. 337.
11. Recent examples: a) P.Hurst, B. K.Takasaki, J. Chin, J. Am. Chem. Soc. 1996, 118, 9982; b) M.J. Young, J. Chin, ibid. 1995, 117, 10577; c) B. Linkletter, J. Chin, Angew. Chem. 1995, 107; 529; Angew. Chem. Int. Ed. Engl. 1995, 34, 472; d) W. H. Chapman, Jr., R. Breslow, J. Am. Chem. Soc. 1995, 117, 5462; e) M. Yashiro, A. Ishikubu, M. Komoyama, J. Chem. Soc. Chem. Commun. 1997, 83; f) M. Yashiro, A. Ishikubu, M. Komiyama, ibid. 1995, 1793; g) M. Komiyama, N. Takeda, M. Irisawa, M. Yashiro in DNA and RNA Cleavers and Chemotherapy of Cancer and Viral Diseases (Ed.: B. Meunier), Kluwer, Boston, 1996, p. 321; h) J. K. Bashkin, J. Xie, A.T. Daniher, L. A. Jenkins, G. C. Yeh, ibid. p. 355-366; i) R. Haner, J. Hall, D. Husken, H. E. Moser, ibid. p. 307; j) D. Magda, R. A. Miller, M. Wright, J. Rao, ibid. p. 337.
12. Recent examples: a) P.Hurst, B. K.Takasaki, J. Chin, J. Am. Chem. Soc. 1996, 118, 9982; b) M.J. Young, J. Chin, ibid. 1995, 117, 10577; c) B. Linkletter, J. Chin, Angew. Chem. 1995, 107; 529; Angew. Chem. Int. Ed. Engl. 1995, 34, 472; d) W. H. Chapman, Jr., R. Breslow, J. Am. Chem. Soc. 1995, 117, 5462; e) M. Yashiro, A. Ishikubu, M. Komoyama, J. Chem. Soc. Chem. Commun. 1997, 83; f) M. Yashiro, A. Ishikubu, M. Komiyama, ibid. 1995, 1793; g) M. Komiyama, N. Takeda, M. Irisawa, M. Yashiro in DNA and RNA Cleavers and Chemotherapy of Cancer and Viral Diseases (Ed.: B. Meunier), Kluwer, Boston, 1996, p. 321; h) J. K. Bashkin, J. Xie, A.T. Daniher, L. A. Jenkins, G. C. Yeh, ibid. p. 355-366; i) R. Haner, J. Hall, D. Husken, H. E. Moser, ibid. p. 307; j) D. Magda, R. A. Miller, M. Wright, J. Rao, ibid. p. 337.
13. Recent examples: a) P.Hurst, B. K.Takasaki, J. Chin, J. Am. Chem. Soc. 1996, 118, 9982; b) M.J. Young, J. Chin, ibid. 1995, 117, 10577; c) B. Linkletter, J. Chin, Angew. Chem. 1995, 107; 529; Angew. Chem. Int. Ed. Engl. 1995, 34, 472; d) W. H. Chapman, Jr., R. Breslow, J. Am. Chem. Soc. 1995, 117, 5462; e) M. Yashiro, A. Ishikubu, M. Komoyama, J. Chem. Soc. Chem. Commun. 1997, 83; f) M. Yashiro, A. Ishikubu, M. Komiyama, ibid. 1995, 1793; g) M. Komiyama, N. Takeda, M. Irisawa, M. Yashiro in DNA and RNA Cleavers and Chemotherapy of Cancer and Viral Diseases (Ed.: B. Meunier), Kluwer, Boston, 1996, p. 321; h) J. K. Bashkin, J. Xie, A.T. Daniher, L. A. Jenkins, G. C. Yeh, ibid. p. 355-366; i) R. Haner, J. Hall, D. Husken, H. E. Moser, ibid. p. 307; j) D. Magda, R. A. Miller, M. Wright, J. Rao, ibid. p. 337.
14. Recent examples: a) P.Hurst, B. K.Takasaki, J. Chin, J. Am. Chem. Soc. 1996, 118, 9982; b) M.J. Young, J. Chin, ibid. 1995, 117, 10577; c) B. Linkletter, J. Chin, Angew. Chem. 1995, 107; 529; Angew. Chem. Int. Ed. Engl. 1995, 34, 472; d) W. H. Chapman, Jr., R. Breslow, J. Am. Chem. Soc. 1995, 117, 5462; e) M. Yashiro, A. Ishikubu, M. Komoyama, J. Chem. Soc. Chem. Commun. 1997, 83; f) M. Yashiro, A. Ishikubu, M. Komiyama, ibid. 1995, 1793; g) M. Komiyama, N. Takeda, M. Irisawa, M. Yashiro in DNA and RNA Cleavers and Chemotherapy of Cancer and Viral Diseases (Ed.: B. Meunier), Kluwer, Boston, 1996, p. 321; h) J. K. Bashkin, J. Xie, A.T. Daniher, L. A. Jenkins, G. C. Yeh, ibid. p. 355-366; i) R. Haner, J. Hall, D. Husken, H. E. Moser, ibid. p. 307; j) D. Magda, R. A. Miller, M. Wright, J. Rao, ibid. p. 337.
15. Recent examples: a) P.Hurst, B. K.Takasaki, J. Chin, J. Am. Chem. Soc. 1996, 118, 9982; b) M.J. Young, J. Chin, ibid. 1995, 117, 10577; c) B. Linkletter, J. Chin, Angew. Chem. 1995, 107; 529; Angew. Chem. Int. Ed. Engl. 1995, 34, 472; d) W. H. Chapman, Jr., R. Breslow, J. Am. Chem. Soc. 1995, 117, 5462; e) M. Yashiro, A. Ishikubu, M. Komoyama, J. Chem. Soc. Chem. Commun. 1997, 83; f) M. Yashiro, A. Ishikubu, M. Komiyama, ibid. 1995, 1793; g) M. Komiyama, N. Takeda, M. Irisawa, M. Yashiro in DNA and RNA Cleavers and Chemotherapy of Cancer and Viral Diseases (Ed.: B. Meunier), Kluwer, Boston, 1996, p. 321; h) J. K. Bashkin, J. Xie, A.T. Daniher, L. A. Jenkins, G. C. Yeh, ibid. p. 355-366; i) R. Haner, J. Hall, D. Husken, H. E. Moser, ibid. p. 307; j) D. Magda, R. A. Miller, M. Wright, J. Rao, ibid. p. 337.
16. Recent examples: a) P.Hurst, B. K.Takasaki, J. Chin, J. Am. Chem. Soc. 1996, 118, 9982; b) M.J. Young, J. Chin, ibid. 1995, 117, 10577; c) B. Linkletter, J. Chin, Angew. Chem. 1995, 107; 529; Angew. Chem. Int. Ed. Engl. 1995, 34, 472; d) W. H. Chapman, Jr., R. Breslow, J. Am. Chem. Soc. 1995, 117, 5462; e) M. Yashiro, A. Ishikubu, M. Komoyama, J. Chem. Soc. Chem. Commun. 1997, 83; f) M. Yashiro, A. Ishikubu, M. Komiyama, ibid. 1995, 1793; g) M. Komiyama, N. Takeda, M. Irisawa, M. Yashiro in DNA and RNA Cleavers and Chemotherapy of Cancer and Viral Diseases (Ed.: B. Meunier), Kluwer, Boston, 1996, p. 321; h) J. K. Bashkin, J. Xie, A.T. Daniher, L. A. Jenkins, G. C. Yeh, ibid. p. 355-366; i) R. Haner, J. Hall, D. Husken, H. E. Moser, ibid. p. 307; j) D. Magda, R. A. Miller, M. Wright, J. Rao, ibid. p. 337.
17. Recent examples: a) P.Hurst, B. K.Takasaki, J. Chin, J. Am. Chem. Soc. 1996, 118, 9982; b) M.J. Young, J. Chin, ibid. 1995, 117, 10577; c) B. Linkletter, J. Chin, Angew. Chem. 1995, 107; 529; Angew. Chem. Int. Ed. Engl. 1995, 34, 472; d) W. H. Chapman, Jr., R. Breslow, J. Am. Chem. Soc. 1995, 117, 5462; e) M. Yashiro, A. Ishikubu, M. Komoyama, J. Chem. Soc. Chem. Commun. 1997, 83; f) M. Yashiro, A. Ishikubu, M. Komiyama, ibid. 1995, 1793; g) M. Komiyama, N. Takeda, M. Irisawa, M. Yashiro in DNA and RNA Cleavers and Chemotherapy of Cancer and Viral Diseases (Ed.: B. Meunier), Kluwer, Boston, 1996, p. 321; h) J. K. Bashkin, J. Xie, A.T. Daniher, L. A. Jenkins, G. C. Yeh, ibid. p. 355-366; i) R. Haner, J. Hall, D. Husken, H. E. Moser, ibid. p. 307; j) D. Magda, R. A. Miller, M. Wright, J. Rao, ibid. p. 337.
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