Hydrolysis of an RNA dinucleoside monophosphate by neomycin B

(Note: The full text of this document is currently only available in the PDF Version )

Sarah R. Kirk and Yitzhak Tor


Abstract

Neomycin B is shown to accelerate the phosphodiester hydrolysis of adenylyl(3′–5′)adenosine (ApA) more effectively than a simple unstructured diamine.


References

  1. For general references discussing RNA hydrolysis, see J. Chin, Acc. Chem. Res., 1991, 24, 145 Search PubMed; R. Breslow, E. Anslyn and D.-L. Huang, Tetrahedron, 1991, 47, 2365 CrossRef CAS; J. Vincent, M. Crowder and B. Averill, TIBS, 1992, 17, 105 CrossRef CAS; E. Anslyn and D. Perreult, Angew. Chem., Int. Ed. Engl., 1997, 36, 430 Search PubMed and references cited therein.
  2. D. Magda, R. A. Miller, J. L. Sessler and B. L. Iverson, J. Am. Chem. Soc., 1994, 116, 7439 CrossRef CAS; K. Matsumura, M. Endo and M. Komiyama, J. Chem. Soc., Chem. Commun., 1994, 2019 RSC; J. Hall, D. Hüsken, U. Pieles, H. E. Moser and R. Häner, Chem. Biol., 1994, 1, 185 CrossRef CAS; J. K. Bashkin, E. I. Frolova and U. Sampath, J. Am. Chem. Soc., 1994, 116, 5981 CrossRef CAS; J. Hall, D. Hüsken and R. Häner, Nucleic Acids Res., 1996, 24, 3522 CrossRef CAS; D. Magda, S. Crofts, A. Lin, D. Miles, M. Wright and J. L. Sessler, J. Am. Chem. Soc., 1997, 119, 2293 CrossRef CAS; D. Magda, M. Wright, S. Crofts, A. Lin and J. L. Sessler, J. Am. Chem. Soc., 1997, 119, 6947 CrossRef CAS.
  3. M. Endo, Y. Azuma, Y. Saga, A. Kuzuya, G. Kawai and M. Komiyama, J. Org. Chem., 1997, 62, 846 CrossRef CAS.
  4. For the hydrolytic cleavage of tRNAPhe by metal-free bleomycin, see M. V. Keck and S. M. Hecht, Biochemistry, 1995, 34, 12 029 Search PubMed.
  5. U. von Ahsen, J. Davies and R. Schroeder, Nature, 1991, 353, 368 CrossRef CAS; U. von Ahsen, J. Davies and R. Schroeder, J. Mol. Biol., 1992, 226, 935 CrossRef CAS; J. Davies, U. von Ahsen and R. Schroeder, The RNA World, ed. R. F. Gesteland and J. F. Atkins, Cold Spring Harbor Laboratory Press, New York, 1993, pp. 185–204 Search PubMed.
  6. T. K. Stage, K. J. Hertel and O. C. Uhlenbeck, RNA, 1995, 1, 95 CAS.
  7. H.-Y. Mei, A. A. Galan, N. S. Halim, D. P. Mack, D. W. Moreland, K. B. Sanders, H. N. Troung and A. W. Czarnik, Bioorg. Med. Chem. Lett., 1995, 5, 2755 CrossRef CAS.
  8. M. L. Zapp, S. Stern and M. R. Green, Cell, 1993, 74, 969 CrossRef CAS; G. Werstuck, M. L. Zapp and M. R. Green, Chem. Biol., 1996, 3, 129 CrossRef CAS.
  9. M. Hendrix, P. B. Alper, E. S. Priestley and C.-H. Wong, Angew. Chem., Int. Ed. Engl., 1997, 36, 95 CrossRef CAS.
  10. H. Wang and Y. Tor, J. Am. Chem. Soc., 1997, 119, 8734 CrossRef CAS; H. Wang and Y. Tor, Bioorg. Med. Chem. Lett., 1997, 7, 1951 CrossRef CAS; H. Wang and Y. Tor, Angew. Chem., in the press Search PubMed.
  11. T. Hermann and E. Westhof, J. Mol. Biol., in the press Search PubMed.
  12. K. Yoshinari, K. Yamazaki and M. Komiyama, J. Am. Chem. Soc., 1991, 113, 5899 CrossRef CAS See also: K. N. Dalby, A. J. Kirby and F. Hollfelder, Pure Appl. Chem., 1994, 66, 687 Search PubMed.
  13. M. Komiyama and K. Yoshinari, J. Org. Chem., 1997, 62, 2155 CrossRef CAS.
  14. B. Barbier and A. Brack, J. Am. Chem. Soc., 1992, 114, 3511 CrossRef CAS.
  15. H. Dugas, Bioorganic Chemistry, A Chemical Approach to Enzyme Action, 2nd edn., Springer Verlag, New York, 1989, pp. 123–137 Search PubMed.
  16. R. E. Botto and B. Coxon, J. Am. Chem. Soc., 1983, 105, 1021 CrossRef CAS See also: D. E. Dorman, J. W. Paschal and K. E. Merkel, J. Am. Chem. Soc., 1976, 98, 6885 Search PubMed; L. Szilágyi, Z. Sz. Pusztahelyi, S. Jakab and I. Kovács, Carbohydr. Res., 1993, 247, 99 CrossRef CAS.
  17. C. P. H. Vary and J. N. Vournakis, Proc. Natl. Acad. Sci. USA, 1984, 81, 6978 CAS; J. M. Kean, S. A. White and D. E. Draper, Biochemistry, 1985, 24, 5062 CrossRef CAS; C. Ehresmann, F. Baudin, M. Mougel, P. Romby, J.-P. Ebel and B. Ehresmann, Nucleic Acids Res., 1987, 15, 9109 CAS; G. Knapp, Methods Enzymol., 1989, 180, 192 CAS; D. S. Sigman and C.-H. Chen, Annu. Rev. Biochem., 1990, 59, 207 CrossRef CAS; D. S. Sigman, A. Mazumder and D. M. Perrin, Chem. Rev., 1993, 93, 2295 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.