Acyl transfer reactions in dipolar aprotic medium: desolvated phosphate ion as acyl acceptor in the formation of energy-rich phosphate compounds

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

Vanderlei Gageiro Machado and Faruk Nome


Abstract

The reaction between an acetate ester and n-decylphosphate ions in dipolar aprotic medium provides a system which allows the facile formation of acetyl phosphate derivatives, by means of restricting the quantities of water available in the reacting system; the role of water is explained in terms of the inhibition of the nucleophilic attack of the phosphate group, which is disfavoured by its presence.


References

  1. F. Lipmann, Adv. Enzymol., 1941, 1, 99 Search PubMed.
  2. H. S. Penefsky and R. L. Cross, Adv. Enzymol. Relat. Areas Mol. Biol., 1991, 64, 173 Search PubMed; P. D. Boyer, Biochim. Biophys. Acta, 1993, 1140, 215 CAS; R. L. Cross, Nature, 1994, 370, 594 CrossRef CAS.
  3. J. P. Abrahams, A. G. W. Leslie, R. Lutter and J. E. Walker, Nature, 1994, 370, 621 CrossRef CAS.
  4. J.-M. Lehn, Angew. Chem., Int. Ed. Engl., 1988, 27, 89 CrossRef; M. W. Hosseini and J.-M. Lehn, J. Chem. Soc., Chem. Commun., 1991, 451 RSC; H. Fenniri and J.-M. Lehn, J. Chem. Soc., Chem. Commun., 1993, 1819 RSC.
  5. L. de Meis, Biochim. Biophys. Acta, 1989, 973, 333 CAS; L. de Meis, Arch. Biochem. Biophys., 1993, 306, 287 CrossRef CAS.
  6. G. Wallerberg and P. Haake, J. Org. Chem., 1981, 46, 43 CrossRef CAS; J. Hajdu and G. M. Smith, J. Am. Chem. Soc., 1981, 103, 6192 CrossRef CAS.
  7. F. Lipmann and L. C. Tuttle, J. Biol. Chem., 1945, 159, 21 CAS.
  8. W. P. Jencks, Chem. Rev., 1972, 72, 705 CrossRef CAS.
  9. F. M. Menger, in Nucleophilicity, ed. J. M. Harris and S. P. McManus, American Chemical Society, Washington, 1987, p. 209 Search PubMed; M. J. S. Dewar and D. M. Storch, J. Chem. Soc., Chem. Commun., 1985, 94 Search PubMed; J. Chandrasekhar, S. F. Smith and W. L. Jorgensen, J. Am. Chem. Soc., 1985, 107, 154 RSC.
  10. G. Di Sabato and W. P. Jencks, J. Am. Chem. Soc., 1961, 83, 4400 CrossRef CAS.
  11. J. Druzian, C. Zucco, M. C. Rezende and F. Nome, J. Org. Chem., 1989, 54, 4767 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.