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Chemistry and Biochemistry of the Amino Acids pp 227–245Cite as

Enzyme Inhibition by Amino Acids and their Derivatives

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Abstract

Over 240 amino acids have been isolated and characterized from bacteria, animals or plants [1]. Only twenty of them are used for protein synthesis. An additional number such as ornithine, citrulline, 5-hydroxytryptophan, dihydroxyphenylalanine and homoserine are intermediates in metabolic processes. Most of the others are much rarer and often localized in a given species where they may be secondary metabolites or, more interestingly, the result of an evolutionary defence mechanism against predators. In addition to those natural amino acids, chemists have made almost innumerable modifications of the most common amino acids. In the present review, only the amino acids either natural or man-made for which the biochemical action has been reported and could be related to the inhibition of a specific enzyme will be mentioned.

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References

  1. Bell, E.A. (1981) Act Chim, 22.

    Google Scholar 

  2. Clark, W.G. (1963) inMetabolic Inhibitors(eds R.M. Hochster and J.H. Quastel) (Vol. 1) Academic Press, New York, London, p. 315.

    Google Scholar 

  3. Sourkes, T.L. (1954)Arch. Biochem. Biophys,51, 444.

    Article  Google Scholar 

  4. Muschol, E. (1972) inHandbuch der Expt. Pharmakologie(eds H. Blaschko and E. Mucholl) (Vol.33, Catecholamines) Springer-Verlag, Berlin and Heidelberg, p. 618.

    Google Scholar 

  5. Shive, W. and Skinner, C.G. (1963) inMetabolic Inhibitors(eds R.M. Hochster and J.H. Quastel), (Vol.1) Academic Press, New York, London, p. 1.

    Google Scholar 

  6. Wolfenden, R. (1972)Acc. Chem. Res,5, 10.

    Article  Google Scholar 

  7. Powers, J.C. (1977)Meth. Enzymol,46, 197.

    Article  Google Scholar 

  8. Baker, B.R. (1967)Design of Active-Site-Directed Irreversible Enzyme Inhibitors, John Wiley and Sons, New York.

    Google Scholar 

  9. Abeles, R.H. and Maycock, A.L. (1976)Acc. Chem. Res,9, 313.

    Article  Google Scholar 

  10. Rando, R.R. (1974)Science,185, 320.

    Article  Google Scholar 

  11. Rando, R.R. (1977)Meth. Enzymol,46, 28.

    Article  Google Scholar 

  12. Seiler, N., Jung, M.J. and Koch-Weser, J. (eds) (1978)Enzyme-Activated Irreversible Inhibitors, Elsevier/North Holland, Amsterdam.

    Google Scholar 

  13. John, R.A. and Fasella, P. (1969)Biochemistry,8, 4477.

    Article  Google Scholar 

  14. Tate, S.S., Relyea, N.M. and Meister, A. (1969)Biochemistry,8, 5016.

    Article  Google Scholar 

  15. Rando, R.R. (1975)Acc. Chem. Res,8, 281.

    Article  Google Scholar 

  16. Sandler, M. (ed) (1980)Enzyme Inhibitors as Drugs, Mac Millan Press, London, Basingstoke.

    Google Scholar 

  17. Dunathan H.C. (1971) inAdv. Enzymol.,35, 79.

    Google Scholar 

  18. Rando, R.R., Relyea, N. and Cheng, L. (1976)J. Biol. Chem 251, 3306.

    Google Scholar 

  19. Marcotte, P. and Walsh, C. (1975)Biochem. Biophys. Res. Commun,62, 677.

    Article  Google Scholar 

  20. Alston, Th. A., Porter, D.J.T., Mela, L. and Bright, H.J. (1980)Biochem. Biophys. Res. Commun,92, 299.

    Article  Google Scholar 

  21. Gehring, H., Rando, R.R. and Christen, Ph. (1977)Biochemistry,16, 4832.

    Article  Google Scholar 

  22. Morino, Y. and Okamoto, M. (1973)Biochem. Biophys. Res. Commun,50, 1061.

    Article  Google Scholar 

  23. Silverman, R. and Abeles, R.H. (1976)Biochemistry,15, 4718.

    Article  Google Scholar 

  24. Walsh, C., Johnston, M., Marcotte, P. and Wang, E. (1978) inEnzyme-Activated Irreversible Inhibitors(eds N. Seiler, M.J. Jung and J. Koch-Weser), Elsevier/North Holland, Amsterdam, p. 177.

    Google Scholar 

  25. Metcalf, B.W., Lippert, B. and Casara, P. (1978) inEnzyme-Activated Irreversible Inhibitors(eds N. Seiler, M.J. Jung and J. Koch-Weser) Elsevier/North Holland, Amsterdam, p. 123.

    Google Scholar 

  26. Fowler, L.J. and John, R.A. (1972)Biochem. J,130, 569.

    Google Scholar 

  27. Bey, P., Jung, M.J. and Gerhart, F.et al(1981)J. Neurochem,37, 1341.

    Article  Google Scholar 

  28. Rando, R.R. (1977)Biochemistry,16, 4604.

    Article  Google Scholar 

  29. Jung M.J. (1980) inEnzyme Inhibitors(ed. U. Brodbeck) Verlag Chemie, Weinheim, p. 85.

    Google Scholar 

  30. Kollonitsch, J. and Barash, L. (1976)J. Amer. Chem. Soc,98, 5591.

    Article  Google Scholar 

  31. Wang, E. and Walsh, C. (1978)Biochemistry,17, 1313.

    Article  Google Scholar 

  32. Jung, M.J. and Koch-Weser, J. (1981) inMolecular Basis of Drug Action(eds. Th.P. Singer and R. Ondaza), Elsevier/North Holland, Amsterdam, p. 135.

    Google Scholar 

  33. Maycock, A. L., Aster, S.D. and Patchett, A.A. (1980)Biochemistry,19, 709.

    Article  Google Scholar 

  34. Owens, L.D., Thompson, J.F., Pitcher, R.G. and Williams, T. (1972)J. Chem. Soc. Chem. Commun., 714.

    Google Scholar 

  35. Washtien, W. and Abeles, R.H. (1977)Biochemistry,16, 2485.

    Article  Google Scholar 

  36. Johnston, M., Marcotte, P., Donovan, J. and Walsh, C. (1979)Biochemistry,18, 1729.

    Article  Google Scholar 

  37. Alston, Th. A., Muramatsu, H., Ueda, T. and Bright, H.J. (1981)FEBS Letters,128, 293.

    Article  Google Scholar 

  38. Johnston, M., Raines, R., Walsh, C. and Firestone, R.A. (1980)J. Amer. Chem. Soc,102, 4241.

    Article  Google Scholar 

  39. Merck and Co. Inc., European Patent 104 805, 1980.

    Google Scholar 

  40. Marcotte, P. and Walsh, C. (1978)Biochemistry,17, 2864.

    Article  Google Scholar 

  41. Dang, T.Y., Cheung, Y.F. and Walsh, C., (1976)Biochem. Biophys. Res. Commun,72, 960.

    Article  Google Scholar 

  42. Yaouanc, J.J., Dugenet, P. and Kraus, J.L. (1979)Pharmacol. Res. Commun,11, 115.

    Article  Google Scholar 

  43. Dmitrienko, G.I., Snieckus, V. and Viswanatha, V. (1977)Bioorganic Chem,6, 421.

    Article  Google Scholar 

  44. Udenfriend, S., Zaltzmann-Nirenberg, P. and Nagatsu, T. (1965)Biochem. Pharmacol,145, 837.

    Article  Google Scholar 

  45. Chang, N., Kaufman, S. and Milstien, S. (1979)J. Biol. Chem,254, 2665.

    Google Scholar 

  46. Okabayashi, K., Morishima, H., Hamada, M. et al. (1977)J. Antibiot,30, 675.

    Google Scholar 

  47. Nicholson, A.N. and Wright, C.M. (1981)Neuropharmacology,20, 335.

    Article  Google Scholar 

  48. Meister, A. (1978) inEnzyme-Activated Irreversible Inhibitors, (eds N. Seiler, M.J. Jung and J. KochWeser), Elsevier/North Holland, Amsterdam, p. 187.

    Google Scholar 

  49. Griffith, O.W. and Meister, A. (1978)J. Biol. Chem,253, 2333.

    Google Scholar 

  50. Griffith, O.W. and Meister, A. (1979)J. Biol. Chem,254, 7558.

    Google Scholar 

  51. Buchanan, J.M. (1978) inEnzyme-Activated Irreversible Inhibitors(eds N. Seiler, M.J. Jung and J. Koch-Weser), Elsevier/North Holland, Amsterdam, p. 277.

    Google Scholar 

  52. Meister, A. (1979) inGlutamic Acid(Advances in Biochemistry and Biophysiology) (eds L.J. Filer, S. Garattini and M.R. Kare), Raven Press, New York, p. 69.

    Google Scholar 

  53. Kinoshita, T., Watanabe, H. and Murato, S. (1981)Bull. Chem. Soc. Jap,54, 2219.

    Article  Google Scholar 

  54. Allen, L., Meck R. and Yunis, A. (1980)Res. Commun. Chem. Pathol. Pharmacol,27, 175.

    Google Scholar 

  55. Jayaram, H.N., Cooney, D.A., Milman, H.A. et al. (1976)Biochem. Pharmacol,25, 1571.

    Article  Google Scholar 

  56. Hirth, C.G., Veron, M., Villar-Palasi, C. et al. (1975)Europ. J. Biochem,50, 425.

    Article  Google Scholar 

  57. Collins, K.D. and Stark, G.R. (1971)J. Biol. Chem,246, 6599.

    Google Scholar 

  58. Morley, J.S. (1980)Rends Pharmacol. Sci., p. 463.

    Google Scholar 

  59. Umezawa, H. (1972)Enzyme Inhibitors of Bacterial Origin, University Park Press, Baltimore, London, Tokyo, p. 14.

    Google Scholar 

  60. Frankfater, A. and Kuppy, T. (1981)Biochemistry,20, 5517.

    Article  Google Scholar 

  61. Almquist, R.G., Chao, W.R., Ellis, M.E. and Johnson, H.L. (1980)J. Med. Chem,23, 1392.

    Article  Google Scholar 

  62. Jacobsen, N.E. and Bartlett, P.A. (1981)J. Amer. Chem. Soc,103, 654.

    Article  Google Scholar 

  63. Shaw, E. (1980) inEnzyme Inhibitors as Drugs, (ed. M. Sandier) MacMillan Press, London, Basingstoke, p. 25.

    Google Scholar 

  64. Green, G.D.J. and Shaw, E. (1981)J. Biol. Chem,256, 1923.

    Google Scholar 

  65. Kanazawa, H. (1977)J. Biochem,81, 1739.

    Google Scholar 

  66. Johnson, R.L. and Poisner, A.M. (1980)Biochem. Biophys. Res. Commun,95, 1404.

    Article  Google Scholar 

  67. Tamai, M., Hanada, K., Adachi, T.et al(1981)J. Biochem,90, 255.

    Google Scholar 

  68. Bechet, J.J., Dupaix, A. and Blagoeva, I. (1977)Biochimie,59, 231.

    Article  Google Scholar 

  69. Krafft, G.A. and Katzenellenbogen, J.A. (1981)J. Amer. Chem. Soc,103, 5459.

    Article  Google Scholar 

  70. White, E.H., Jelinski, L.W., Politzer, E.R.et al(1981)J. Amer. Chem. Soc,103, 4231.

    Article  Google Scholar 

  71. Ondetti~ MA., Cushman, D.W., Sabo, E.F.et al(1981) inMolecular Basis of Drug Action, (eds. Th. P. Singer and R. Ondarza), Elsevier/North Holland, Amsterdam, p. 235.

    Google Scholar 

  72. Gross, D.M., Sweet, C.S., Ulm, E.H.et al(1981)J. Pharmacol. Exp. Therap,216, 552.

    Google Scholar 

  73. Barrett, A.J. (1980) inEnzyme Inhibitors as Drugs, (ed. M. Sandler) MacMillan Press, London, Basingstoke, p. 219.

    Google Scholar 

  74. Roques, B.P., Fournie-Zaluski, M.C., Soroca, E.et al(1980)Nature,288, 286.

    Article  Google Scholar 

  75. Casara, P., Danzin, C., Metcalf, B.W. and Jung, M.J. (1982) J. Chem. Soc., Chem. Commun. 1190.

    Google Scholar 

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Authors
  1. M. J. Jung
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  1. Oxford Polytechnic, UK

    G. C. Barrett

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© 1985 Chapman and Hall

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Jung, M.J. (1985). Enzyme Inhibition by Amino Acids and their Derivatives. In: Barrett, G.C. (eds) Chemistry and Biochemistry of the Amino Acids. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-4832-7_7

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  • DOI: https://doi.org/10.1007/978-94-009-4832-7_7

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-010-8642-4

  • Online ISBN: 978-94-009-4832-7

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