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The Shikimate Pathway

  • Heinz G. Floss
Part of the Recent Advances in Phytochemistry book series (RAPT, volume 12)

Abstract

The shikimate pathway is the major metabolic route leading to the formation of aromatic compounds in living systems. It operates in microorganisms and in higher plants, but not in animals, which is why the latter are dependent on a dietary supply of the aromatic amino acids phenylalanine, tyrosine and tryptophan. In addition to providing these essential protein constituents, the shikimate pathway is necessary for the synthesis of essential cofactors, like folic acid or various isoprenylated quinones, and of the important structural material, lignin, and it is involved in the formation of a vast array of so-called secondary metabolites in plants and microorganisms, like phenylpropanoids, alkaloids or many antibiotics.

Keywords

Shikimic Acid Quinic Acid Shikimate Pathway COOH COOH Claisen Rearrangement 
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.

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References

  1. 1.
    Bentley, R. 1975. In “Biosynthesis”, T.A. Geissman, Ed., Specialist Periodical Reports, The Chemical Society, London. Vol. 3, p. 181–246.Google Scholar
  2. 2.
    Bondinell, W.E., J. Vnek, P.K. Knowles, M. Sprecher, D. B. Sprinson. 1971.J. Biol. Chem.246, 6191.Google Scholar
  3. 3.
    Butler, J.R., W.L. Alworth, M.J. Nugent. 1974.J.Amer.Chem.Soc.96, 1617.CrossRefGoogle Scholar
  4. Campbell, I.M. 1969.Tetrahedron Letters4777.Google Scholar
  5. 5.
    Cornforth, J.W., J.W. Redmond, H. Eggerer, W. Buckel, C. Gutschow. 1970.Europ.J.Biochem.14, 1.PubMedCrossRefGoogle Scholar
  6. 6.
    Danishefsky, S., M. Hirama, 1977. Unpublished results.Google Scholar
  7. 7.
    Dansette, P., R. Azerad. 1970.Biochem.Biophys.Res.Comm.40, 1090.Google Scholar
  8. 8.
    Dardenne, G.A., P.O. Larsen, E. Wieczorkowska. 1975.Biochim.Biophys.Acta 381, 416.Google Scholar
  9. 9.
    Dardenne, G.A., M. Marlier, J. Casimir. 1972.Phytochemistry 11, 2567.CrossRefGoogle Scholar
  10. 10.
    DeLeo, A.B., J. Dayan, D.B. Sprinson. 1973.J.Biol.Chem.248, 2344.Google Scholar
  11. 11.
    DeLeo, A.B., D.B. Sprinson. 1968.Biochem.Biophys.Res.Comm. 373.Google Scholar
  12. 12.
    Dunathan, H.C. J.G. Voet. 1974.Proc.Nat.Acad.Sei.71, 3888.Google Scholar
  13. 13.
    Emes, A., H.G. Floss, D.A. Lowe, D.W.S. Westlake, L.C. Vining. 1974.Can.J.Microbiol. 347.Google Scholar
  14. 14.
    Evans, J.A. M.A. Osman. 1974.Nature 250, 348PubMedCrossRefGoogle Scholar
  15. 15.
    Farrfsworth, N.R., A.S. Bingel, H.H.S. Fong, A.A. Saleh, G.M. Christenson, S.M. Saufferer. 1976.Cancer Treatment Reports 60, 1171.Google Scholar
  16. 16.
    Floss, H.G., D.K. Onderka, M. Carroll. 1972.J.Biol.Chem.247, 736.Google Scholar
  17. 17.
    Fuganti, C., D. Ghiringhelli, D. Giangrasso, P. Grasselli, A.S. Amisano. 1974.Chimica e Industria 56, 424.Google Scholar
  18. 18.
    Gibson, F., M. Gibson, G.B. Cox. 1964.Biochim.Biophys.Acta 82, 637.Google Scholar
  19. 19.
    Gibson, M.I., F. Gibson. 1962.Biochim.Biophys.Acta 65,160.Google Scholar
  20. 20.
    Gross, S.R. 1958.J.Biol.Chem.233, 1146.Google Scholar
  21. 21.
    Hadwiger, L., H.G. Floss, J.R. Stocker, E.E. Conn. 1965.Phytochemistry 4, 825.CrossRefGoogle Scholar
  22. 22.
    Hanson, K.R., I.A. Rose. 1963.Proc.Nat.Acad.Sei.50, 981.CrossRefGoogle Scholar
  23. 23.
    Haslam, E. 1974. “The Shikimate Pathway”, John Wiley and Sons, New York-Toronto.Google Scholar
  24. 24.
    Herrmann, K.M., M.D. Poling. 1975.J.Biol.Chem.250, 6817Google Scholar
  25. 25.
    Hill, R.K., G.R. Newkome. 1969.J.Amer.Chem.Soc. 5893Google Scholar
  26. 26.
    Hook, D.K., G.F. Warner, K. Shimada, H.G. Floss. 1977. Unpublished results.Google Scholar
  27. 27.
    Hornemann, U., J.E.Eggert. 1977. Unpublished results.Google Scholar
  28. 28.
    Hornemann, U., J.P. Kehrer, J.E. Eggert. 1974.Chem.Google Scholar
  29. Comm.1045.Google Scholar
  30. Jacobsen, L.B., C.A. Richardson, H.G. Floss, unpublished results.Google Scholar
  31. 30.
    Johnson, R.D., A. Haber, K.L. Rinehart. 1974.J.Amer.Chem.Soc.96, 3316.Google Scholar
  32. 31.
    Karlsson, A., G. Sartori, R.J. White. 1974.Europ.J.Biochem.47, 251.PubMedCrossRefGoogle Scholar
  33. 32.
    Knowles, P.F., R.D. Haworth, E. Haslam. 1961.J.Chem.Soc.1954.Google Scholar
  34. 33.
    Larsen, P.O. 1967.Biochim.Biophys.Acta 141, 27.Google Scholar
  35. 34.
    Larsen, P.O., D.K. Onderka, H.G. Floss. 1975.Biochim.Biophys.Acta 381, 397.Google Scholar
  36. 35.
    Morino, Y., E.E. Snell. 1976. J.Biol.Chem.242, 2800.Google Scholar
  37. 36.
    Patel, N. D.L. Pierson, R.A. Jensen. 1977. J.Biol.Chem.252, 5839.Google Scholar
  38. 37.
    Pilch, P.F., R.L. Somerville. 1976.Biochemistry 15, 5315.PubMedCrossRefGoogle Scholar
  39. 38.
    Rose, I.A. 1972.Grit.Rev.Bio chem.1, 33.Google Scholar
  40. 39.
    Rothenberg, S.L., D.B. Sprinson. 1970.Proc.Nat.Acad.Sei. 1669.Google Scholar
  41. 40.
    Scannen, J.P., D.L. Pruess, T.C. Demney, T. Williams, A. Stempel. 1970.J.Antibiot.23, 618.CrossRefGoogle Scholar
  42. 41.
    Scharf, K.H., M.H. Zenk, D.K. Onderka, M. CarroU, H.G. Floss. 1971.Chem.Comm.765.Google Scholar
  43. 42.
    Schleicher, E., K. Mascaro, R. Potts, D.R. Mann, H.G. Floss. 1976. J.Amer.Chem.Soc.98, 1043.Google Scholar
  44. 43.
    Shimada, K., H.G. Floss. 1977. Unpublished resultsGoogle Scholar
  45. 43a.
    Skye, G.E, R. Potts, H.G. Floss. 1974. J.Amer.Chem.Soc.96, 1593.CrossRefGoogle Scholar
  46. 44.
    Stenmark, S.L., D.L. Pierson, G.I. Glover, R.A. Jensen. 1974.Nature 247, 290.PubMedCrossRefGoogle Scholar
  47. Tsai, M.-D., H.G. Floss. Unpublished results.Google Scholar
  48. 46.
    M.J. Turner, B.W. Smith, E. Haslam. 1975.J.C.S. Perkin I, 52.Google Scholar
  49. 47.
    Vaz, A.D.N., J.R. Butler, M.J. Nugent. 1975.J.Amer.Chem.Soc.97, 5914.Google Scholar
  50. 48.
    Vining, L.C. V.S. Malik, D.W.S. Westlake. 1968.Lloydia 31, 355.Google Scholar
  51. 49.
    White, R.J., E. Martinelli. 1974.FEES Letters 49, 233.CrossRefGoogle Scholar
  52. 50.
    Yanofsky, C., J.P. Crawford. 1972. P.D. Boyer, Ed. “The Enzymes”, 3rd Ed., Academic Press, New York, Vol. VII, p. 1–31.Google Scholar
  53. 51.
    Young, J.G. 1975.Biochemistry 14, 399.PubMedCrossRefGoogle Scholar
  54. 52.
    Zenk, M.H. 1965. In “Biosynthesis of Aromatic Compounds”, G. Billek, Ed., Pergamon Press, Oxford.Google Scholar
  55. 53.
    Zenk, M.H., E. Leistner. 1968.Lloydia 31, 275.Google Scholar

Copyright information

© Plenum Press, New York 1979

Authors and Affiliations

  • Heinz G. Floss
    • 1
  1. 1.Department of Medicinal Chemistry and Pharmacognosy School of Pharmacy and Pharmacal SciencesPurdue UniversityIndianaUSA

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