Photo-regulation of RNA hydrolysis by the zinc(II) complex carrying azobenzene

Chemistry Letters

Volumn , Issue 5, 1999, Pages 439-440

  Sumaoka, Jun ^a   Kawata, Kentaro ^a   Komiyama, Makoto ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0033242016     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1999.439     Document Type: Article

References (21)

1. Reviews: a) B. N. Trawich, A. T. Daniher, and J. K. Bashkin, Chem. Rev., 98, 939 (1998).
2. b) M. Oivanen, S. Kuusela, and H. Lönnberg, Chem. Rev., 98, 961 (1998).
3. c) G. Pratviel, J. Bernadou, and B. Meunier, in "Advances in Inorganic Chemistry," ed by A. G. Sykes, Academic Press, San Diego (1998), Vol. 45, pp. 251-312.
4. d) J. Chin, Curr. Opin. Chem. Biol., 1, 514 (1997).
5. e) M. Komiyama and J. Sumaoka, Curr. Opin. Chem. Biol., 2, 751 (1998).
6. The transition state for RNA hydrolysis is more negatively charged than is the initial state, and thus is stabilized in a greater extent by the adjacent positive charge: H. Dugas, C. Penney, "Bioorganic Chemistry," Springer-Verlag, New York (1981), pp. 108-135.
7. Photo-isomerization of azobenzene was previously used to modulate guest-binding activities of host molecules and also to alter the structures of molecular assemblies: a) S. Shinkai, T. Minami, Y. Kusano, and O. Manabe, J. Am. Chem. Soc., 105, 1851 (1983).
8. b) F. Würthner and J. Rebek, Jr., J. Chem. Soc., Perkin Trans. 2, 1995, 1727.
9. c) M. Shimomura and T. Kunitake, J. Am. Chem. Soc., 109, 5175 (1987).
10. Enzymatic activities were photo-controlled by incorporating an azobenzene near the active center: a) I. Willner, S. Rubin, and A. Riklin, J. Am. Chem. Soc., 113, 3321 (1991).
11. b) I. Hamachi, T. Hiraoka, Y. Yamada, and S. Shinkai, Chem. Lett. 1998, 537-538.
12. Various Zn(II) complexes hydrolyzing RNA and other phosphoesters were reported: a) W. H. Chapmann, Jr. and R. Breslow, J. Am. Chem. Soc., 117, 5462 (1995).
13. b) T. Koike, M. Inoue, E. Kimura, and M. Shiro, J. Am. Chem. Soc., 118, 3091 (1996).
14. c) M. Yashiro, A. Ishikubo, and M. Komiyama, Chem. Commun. 1997, 83.
15. d) P. Molenveld, J. F. J. Engbersen, H. Kooijman, A. L. Spek, and D. N. Reinhoudt, J. Am. Chem. Soc., 120, 6726 (1998), and references cited therein.
16. J. Huuskonen, J. Schulz, E. Kolehmainen, and K. Rissanen, Chem. Ber., 127, 2267 (1994).
17. The 3′-monophosphate was predominantly (>90%) formed over the 2′-monophosphate. The 2′,3′-cyclic monophosphate was rapidly hydrolyzed and not much accumulated.
18. -1.
19. More than 99% of the Zn(II) ions in the reaction mixture form complexes with either of the two BPA residues of 1, as estimated from the binding constant of the 1:1 Zn(II)/BPA complex; "Stability Constants of Metal-Ion Complexes, Supplement No. 1 Special Publication 25," ed by A. E. Martell, The Chemical Society, Burlington House, London (1971), part II, p. 678.
20. For each of the isomers, two types of aromatic signals were observed, as reported for 4,4′-bis(iminodiacetic acid)azobenzene: M. Blank, L. M. Soo, N. H. Wassermann, and B. F. Erlanger, Science, 214, 70 (1981).
21. For the cooperative catalysis, the distance must be 3-5 Å (see Ref. 1d).