View PDF Version
 
DOI: 10.1039/A809809C (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1999, 849-854

Synthesis of 4-deoxyquinic, 4-deoxyshikimic and 4-deoxy-3-dehydroshikimic acids

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

Concepción González-Bello, John R. Coggins, Alastair R. Hawkins and Chris Abell

Abstract

The synthesis of 4-deoxyquinic acid (1b) from (–)-quinic acid (1a) and 4-deoxyshikimic acid (4b) from shikimic acid (4a) respectively are described. 4-Deoxyshikimic acid (4b) was converted enzymatically into 4-deoxy-3-dehydroshikimic acid (3b) using shikimate dehydrogenase. The C(4) hydroxy group is shown not to contribute significantly to substrate specificity for shikimate dehydrogenase. Attempts to synthesise 4-deoxy-3-dehydroquinic acid (2b) are described.

References

  1. R. Bentley, CRC Crit. Rev. Biochem., 1990, 25, 307 Search PubMed.
  2. R. McCrindle, K. H. Overton and R. A. Raphael, J. Chem. Soc., 1960, 1560 RSC.
  3. H. C. Steinrucken and N. Amhrein, Biochem. Biophys. Res. Commun., 1980, 94, 1207 CAS.
  4. F. Roberts, C. W. Roberts, J. J. Johnson, D. E. Kyle, T. Krell, J. R. Coggins, G. H. Coombs, W. K. Milhous, S. Tzipori, D. J. P. Ferguson, D. Chakrabarti and R. McLeod, Nature, 1998, 393, 801 CrossRef CAS.
  5. J. M. Harris, W. J. Watkins, A. R. Hawkins, J. R. Coggins and C. Abell, J. Chem. Soc., Perkin Trans. 1, 1996, 2371 RSC.
  6. T. D. H. Bugg, C. Abell and J. R. Coggings, Tetrahedron Lett., 1988, 29, 6779 CrossRef CAS.
  7. M. K. Manthey, C. González-Bello and C. Abell, J. Chem. Soc., Perkin Trans. 1, 1997, 625 RSC.
  8. D. Desmale and S. Tanier, Tetrahedron Lett., 1985, 26, 4941 CrossRef.
  9. L. A. Sarandeses, J. L. Mascareñas, L. Castedo and A. Mouriño, Tetrahedron Lett., 1992, 37, 5445 CrossRef CAS.
  10. M. Díaz, J. Ibarzo, J. M. Jiménez and R. M. Ortuño, Tetrahedron: Asymmetry, 1994, 5, 129 CrossRef CAS.
  11. (a) B. W. Smith, M. J. Turner and E. Haslam, J. Chem. Soc., Chem. Commun., 1970, 842 Search PubMed; (b) E. Haslam, M. J. Turner, D. Sargent and R. S. Thompson, J. Chem. Soc. (C), 1971, 1489 RSC.
  12. (a) R. Grewe and J. P. Jeschke, Chem. Ber., 1956, 89, 2080 CAS; (b) R. Grewe and H. Haendler, Biochem. Prep., 1968, 11, 21 Search PubMed.
  13. S. Mitsuhashi and B. D. Davis, Biochim. Biophys. Acta, 1954, 15, 54 CAS.
  14. E. J. Parker, A. R. Hawkins and C. Abell, unpublished results.
  15. W. L. F. Armarego and D. D. Perrin, Purification of Laboratory Chemicals, Butterworth Heinemann, Oxford, 4th edn., 1996 Search PubMed.
  16. (a) J. D. Moore, H. K. Lamb, T. Garbe, S. Servos, G. Dougan, I. G. Charles and A. R. Hawkins, Biochem. J., 1992, 287, 173 CAS; (b) D. G. Gourlay, J. R. Coggins, N. W. Isaacs, J. D. Moore, I. G. Charles and A. R. Hawkins, J. Mol. Biol., 1994, 241, 488 CrossRef; (c) A. R. Hawkins and M. Smith, Eur. J. Biochem., 1991, 196, 717 CAS.
  17. S. Chaudhuri, I. A. Anton and J. R. Coggins, Methods Enzymol., 1987, 142, 315 CAS.
  18. S. Chaudhuri and J. R. Coggins, Biochem. J., 1985, 226, 217 CAS.