Advertisement

Catalysis of the oligomerization of O-phospho-serine, aspartic acid, or glutamic acid by cationic micelles

  • Christof Böhler
  • Aubrey R. HillJr.
  • Leslie E. Orgel
Article

Abstract

Treatment of relatively concentrated aqueous solutions of O-phospho-serine (50 mM), aspartic acid (100 mM) or glutamic acid (100 mM) with carbonyldiimidazole leads to the formation of an activated intermediate that oligomerizes efficiently. When the concentration of amino acid is reduced tenfold, few long oligomers can be detected. Positively-charged cetyltrimethyl ammonium bromide micelles concentrate the negatively-charged activated intermediates of the amino acids at their surfaces and catalyze efficient oligomerization even from dilute solutions.

Keywords

Ammonium Aqueous Solution Bromide Organic Chemistry Catalysis 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Armstrong, D. W., Seguin, R., McNeal, C. J., Macfarlane, R. D. and Fendler, J. H.: 1978,J. Am. Chem. Soc. 100, 4605–4606.Google Scholar
  2. Broxton, T. J. and Lucas, M.: 1994,J. Phys. Org. Chem. 7, 442–447.Google Scholar
  3. Ehler, K. W.: 1976,J. Org. Chem. 41, 3041–3042.Google Scholar
  4. Ehler, K. W., Girard, E. and Orgel, L. E.: 1977,Biochim. Biophys. Acta 491, 253–264.PubMedGoogle Scholar
  5. Ehler, K. W. and Orgel, L. E.: 1976,Biochim. Biophys. Acta 434, 233–243.PubMedGoogle Scholar
  6. Engbersen, J. F. J., Koudijs, A. and Vanderplas, H. C.: 1990,J. Mol. Cat. 57, 417–426.Google Scholar
  7. Fendler, J. H. and Fendler, E. J.: 1975,Catalysis in Micellar and Macromolecular systems. Academic Press, New York.Google Scholar
  8. Joyce, G. F., Inoue, T. and Orgel, L. E.: 1984,J. Mol. Biol. 176, 279–306.PubMedGoogle Scholar
  9. Menger, F. M.: 1991,Angew. Chem. 103, 1104–1118.Google Scholar
  10. Menger, F. M. and Fei, Z. X.: 1994,Angew. Chem. 33, 346–348.Google Scholar
  11. Oparin, A. I.: 1924, Proischogdenie Zhizni. Translation in J.D. Bernal (1967) “The Origin of Life”, London, Weidenfeld and Nicolson; World Publishing Co., New York. Moscovsky Robotchii, Moscow.Google Scholar
  12. Panigrahi, G. P. and Mishra, S. K.: 1993,J. Mol. Cat. 81, 349–362.Google Scholar
  13. Patel, M. S., Bijma, K. and Engberts, J. B. F. N.: 1994,Langmuir 10, 2491–2492.Google Scholar
  14. Zieboll, G. and Orgel, L. E.: 1994,J. Mol. Evol. 38, 561–565.PubMedGoogle Scholar

Copyright information

© Kluwer Academic Publishers 1996

Authors and Affiliations

  • Christof Böhler
    • 1
  • Aubrey R. HillJr.
    • 1
  • Leslie E. Orgel
    • 1
  1. 1.The Salk Institute for Biological StudiesSan DiegoUSA

Personalised recommendations