Gold(III)-induced oxidation of glycine†

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Juan Zou, Zijian Guo, John A. Parkinson, Yu Chen and Peter J. Sadler


Abstract

NMR investigations of isotopically-labelled glycine show that AuIII induces deamination and subsequent decarboxylation of the amino acid with formation of glyoxylic acid, NH4+, formic acid, CO2 and metallic gold.


References

  1. C. F. Shaw III, Perspect. Biol. Med., 1979, 2, 287 Search PubMed ; P. J. Sadler, Struct. Bonding (Berlin), 1976, 29, 171 CAS ; K. C. Dash and H. Schmidbaur, Met. Ions Biol. Syst., 1983, 14, 180 Search PubMed ; P. J. Sadler and R. E. Sue, Metal-Based Drugs, 1994, 1, 107 Search PubMed .
  2. C. F. Shaw III, Comments Inorg. Chem., 1989, 8, 233 ; S. L. Best and P. J. Sadler, Gold Bull., 1996, 29, 87 Search PubMed .
  3. E. Gleichmann, D. Schuhmann and M. Kubickamuranyi, Eur. J. Pharmacol., 1990, 183, 78 CrossRef .
  4. C. F. Shaw III, S. Schraa, E. Gleichmann, Y. P. Grover, L. Dunemann and A. Jagarlamudi, Metal-Based Drugs, 1994, 1, 351 Search PubMed ; K. Takahashi, P. Griem, C. Goebel, J. Gonzalez and E. Gleichmann, Metal-Based Drugs, 1994, 1, 483 Search PubMed .
  5. R. V. Parish, B. P. Howe, J. P. Wright, J. Mack, R. G. Pritchard, R. G. Buckley, A. M. Elsome and S. P. Fricker, Inorg. Chem., 1996, 35, 1659 CrossRef CAS ; P. Calamai, S. Carotti, A. Guerri, T. Mazzei, L. Messori, E. Mini, P. Orioli and G. P. Speroni, Anti-Cancer Drug Des., 1998, 13, 67 Search PubMed .
  6. C. F. Shaw III, M. P. Cancro, P. L. Witkiewicz and J. E. Eldridge, Inorg. Chem., 1980, 19, 3198 CrossRef ; P. L. Witkiewicz and C. F. Shaw III, J. Chem. Soc., Chem. Commun., 1981, 1111 RSC .
  7. D. H. Brown and W. E. Smith, Am. Chem. Soc. Symp. Ser., 1983, 209, 401 Search PubMed ; W. E. Smith and J. Reglinski, Perspect. Bioinorg. Chem., 1991, 1, 183 Search PubMed .
  8. E. Bordignon, L. Cattalini, G. Natile and A. Scatturi, J. Chem. Soc., Chem. Commun., 1973, 878 RSC ; G. Natile, E. Bordignon and L. Cattalini, Inorg. Chem., 1976, 15, 246 CrossRef CAS ; A. A. Isab and P. J. Sadler, Biochim. Biophys. Acta, 1979, 492, 322 .
  9. To view supplementary data in electronic form see: http://www.rsc.org/suppdata/cc/1999/1359. .
  10. S. J. Berners-Price and P. J. Sadler, Coord. Chem. Rev., 1996, 151, 1 CrossRef CAS  and references therein.
  11. Y. Chen, Z. Guo, P. del S. Murdoch, E. Zang and P. J. Sadler, J. Chem. Soc., Dalton Trans., 1998, 1503 RSC .
  12. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, ed. J. March, John Wiley & Sons, New York, 1985, p. 784 Search PubMed .
  13. Critical Stability Constants, ed. A. E. Martell and R. M. Smith, Plenum Press, New York, 1977, p. 65 Search PubMed .
  14. T. C. Stringfellow, G. Wu and R. E. Wasylishen, J. Phys. Chem. B, 1997, 101, 9651 CrossRef CAS .
  15. R. B. Calvert and J. R. Shapley, J. Am. Chem. Soc., 1978, 100, 7726 CrossRef CAS .
  16. F. A. L. Anet and A. H. Dekmezian, J. Am. Chem. Soc., 1979, 101, 5449 CrossRef CAS .
  17. L. H. Skibsted and J. Bjerrum, Acta Chem. Scand., Ser. A, 1974, 28, 740 .
  18. B. S. Maritz and R. van Eldik, J. Inorg. Nucl. Chem., 1976, 38, 1749 CrossRef CAS .
  19. NMR of Proteins and Nucleic Acids, ed. K. Wüthrich, John Wiley & Sons, New York, 1986, p. 24 Search PubMed .
  20. M.-C. Rodriguez, F. Lambert, I. Morgenstern-Badarau, M. Cesario, J. Guilhem, B. Keita and L. Nadjo, Inorg. Chem., 1997, 36, 3525 CrossRef CAS .
  21. V. Balzani, V. Carassiti, V. Moggi and N. Sabbatini, Inorg. Chem., 1965, 4, 1247 CrossRef CAS .
  22. M. J. Sima, Chem. Pap.—Chem. Zvesti., 1997, 51, 258 Search PubMed .
  23. S. L. Best, Ph. D. thesis, University of London, 1996 .
  24. N. Kratochwil, Z. Guo, P. del S. Murdoch, J. A. Parkinson, P. J. Bednarski and P. J. Sadler, J. Am. Chem. Soc., 1998, 120, 8253 CrossRef CAS ; Y. Chen, Z. Guo, J. A. Parkinson and P. J. Sadler, J. Chem. Soc., Dalton Trans., 1998, 3577 RSC .
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