Advertisement

Enzymatic Modification of β-Lactam Antibiotics: Problems and Perspectives

  • V. K. Svedas
  • A. L. Margolin
  • I. V. Berezin

Abstract

β-Lactam antibiotics make up a large group of physiologically active compounds including natural and semisynthetic penicillins, Cephalosporins, and cephamycins. Many of them are characterized by unique antimicrobial properties, bacteriocidal action, and low toxicity and are widely used for practical applications in medicine. Because of their practical effectiveness, the synthesis of β-lactam antibiotics is a major problem of present interest. Many fine mechanisms of the molecular action of penicillins and Cephalosporins already have been investigated (1, 2). But despite great success in this field, it is difficult to select the structure and predict the properties of new β-lactam antibiotics. In connection with this one cannot but mention the great variety of these compounds, several tens of thousands at present.

Keywords

Enzymatic Synthesis Phenylacetic Acid Gibbs Free Energy Change Acyl Moiety Gibbs Energy Change 
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. 1.
    Strominger, J. L., Willoughby, E., Kamizyo, T., Blumberg, P. & Yocum, R. Ann. N. Y. Acad. Sci. 235: 210, 1974.CrossRefGoogle Scholar
  2. 2.
    Dusart, J., Leyh-Bouille, M., & Ghuysen, Y-M. Eur. J. Biochem. 81: 33, 1977.CrossRefGoogle Scholar
  3. 3.
    Berezin, I.V., Klyosov, A. A., Nys, P.S., Savitskaya, Ye. M. & Svedas, V. K. Antibiotiki (Russ.) 19: 880, 1974.Google Scholar
  4. 4.
    Svedas, V. K., Klyosov, A. A., Nys, P. S., Savitskaya, Ye. M. & Berezin, I. V. Antiblotiki (Russ.) 21: 698, 1976.Google Scholar
  5. 5.
    Warburton, D., Balasingham, K., Dunnill, P. & Lilly, M.D. Biochim. Biophys. Acta 284: 278, 1972.Google Scholar
  6. 6.
    Carrington, T. R. Proc. Roy. Soc. B 179: 321, 1971.CrossRefGoogle Scholar
  7. 7.
    Dinelli, D. Process Biochem. 7: 9, 1972.Google Scholar
  8. 8.
    Vandamme, E. J. & Voets, J. P. Adv. Appl. Microbiol. 17: 311, 1974.CrossRefGoogle Scholar
  9. 9.
    Loder, B. & Newton, G. G. F. Biochem. J. 79: 408, 1961.Google Scholar
  10. 10.
    Svedas, V. K. In “Immobilizovannye Fermenty” (“Immobilized Enzymes”, Russ.) I. V. Berezin, V. K. Ntonov, and K. Martinek eds.) Moscow University Press, Moscow, 1975, p. 221.Google Scholar
  11. 11.
    Manhas, M. S. & Bose, A. K. “Synthesis of Penicillin, Cephalosporin and Analogs,” Marcel Dekker, New York, 1969.Google Scholar
  12. 12.
    Batchelor, F. R. & Cameron-Wood, J. Nature 195: 1000, 1962.CrossRefGoogle Scholar
  13. 13.
    Anon., Recommendation for Measurement and Presentation of Biochemical Equilibrium Data” J. Biol. Chem. 251: 6879, 1976.Google Scholar
  14. 14.
    Svedas, V. K., Margolin, A. L., Galaev, I. Yu. & Berezin, I.V. In “Proceedings Third Joint Us/Ussr Enzyme Engineering Seminar Us/Ussr Joint Working Group on Production of Substances by Microbiological Means”, 1978, p. 679.Google Scholar
  15. 15.
    Svedas, V. K., “Kinetics and Mechanism of the Action of Penicillin Amidase,” Candidate of Chemical Sciences Dissertation, Moscow, 1976.Google Scholar
  16. 16.
    Berezin, I. V., Klyosov, A. A., Margolin, A. L., Nys, P. S., Savitskaya, Ye. M. & Svedas, V. K. Antiblotiki (Russ.) 21: 511, 1976.Google Scholar
  17. 17.
    Klyosov, A. A., Margolin, A. L. & Svedas, V. K. Bioora. Khim. (Russ.) 3: 654, 1977.Google Scholar
  18. 18.
    Berezin, I. V., Margolin, A. L. & Svedas, V. K. Dokl. Acad. Nauk. Ussr (Russ.) 5: 1127, 1977.Google Scholar
  19. 19.
    Margolin, A. L. & Svedas, V. K. In “Second National Symposium on Production and Use of Immobilized Enzymes,” Abstracts (Russ.), Abovyan, 1977, p. 34.Google Scholar
  20. 20.
    Margolin, A. L., Svedas, V. K., Nys, P. S., Koltsova, Ye. V., Savitskaya, Ye. M. & Berezin, I. V. Antibiotiki (Russ.) 23: 114, 1978.Google Scholar
  21. 21.
    Margolin, A. L. & Svedas, V. K. In “Second National Symposium on Microbial Enzymes”, vol. 1, Abstracts (Russ.), Minsk, 1978, p. 158.Google Scholar
  22. 22.
    Margolin, A. L. “Kinetic and Thermodynamic Regularities of Enzymatic Synthesis of β-Lactam Antibiotic Catalyzed by Penicillin Amidase”, Candidate of Chemical Sciences Disservation, Moscow, 1979.Google Scholar
  23. 23.
    Berezin, I. V., Klyosov, A. A., Margolin, A. L., Nys, P. S., Savitskaya, Ye. M. & Svedas, V. K., Antibiotiki (Russ.) 21: 411, 1976.Google Scholar
  24. 24.
    Svedas, V. K., Margolin, A. L., Sherstiuk, S. F. & Berezin, I.V. In “Third National Symposium on Structure and Functions of Active Sites of Enzymes”, Abstracts (Russ.) Pushino, 1976, p. 24.Google Scholar
  25. 25.
    Svedas, V. K., Margolin, A. L., Sherstiuk, S. F. & Berezin, I. V. Dokl. Acad. Nauk Sssr (Russ.) 232: 1127, 1977.Google Scholar
  26. 26.
    Svedas, V. K., Margolin, A. L., Sherstiuk, S. F. & Berezin, I. V. Bioorg. Khim. 3: 546, 1977.Google Scholar
  27. 27.
    Margolin, A. L. & Svedas, V. K. In “Second National Symposium on Production and Use of Immobilized Enzymes”, Abstracts (Russ.) Abovyan, 1977, p. 154.Google Scholar
  28. 28.
    Cole, M. Biochem. J. 115: 741, 1969.Google Scholar
  29. 29.
    Cole, M. Biochem. J. 115: 747, 1969.Google Scholar
  30. 30.
    Svedas, V. K., Klyosov, A. A., Berezin, I. V., Rotangva, T. V., Vasilyeva, N. V., Ginodman, L. M. & Antonov, V. K. In “Third National Symposium on Structure and Functions of Active Sites of Enzymes”, Abstract (Russ.), Pushino, 1976, p. 25.Google Scholar
  31. 31.
    Klyosov, A. A., Galaev, I. U. & Svedas, V. K. Bioorg. Khim. (Russ.) 3: 663, 1977.Google Scholar
  32. 32.
    Klyosov, A. A., Svedas, V. K. & Galaev, I. U. Bloorg. Khim. (Russ.) 3: 800, 1977.Google Scholar
  33. 33.
    Carpenter, F. H. J. Amer. Chem. Soc. 82: 1111, 1960.CrossRefGoogle Scholar
  34. 34.
    Fersht, A. R. & Requena, Y. J. Amer. Chem. Soc. 93: 3499, 1971.CrossRefGoogle Scholar
  35. 35.
    Dyachenko, Ye. D., Kozlov, L. V. & Antonov, V. K. Bioorg. Khim. (Russ.) 3: 99, 1977.Google Scholar
  36. 36.
    Antonov, V. K., Ginodman, L. M. & Gurova, A. G. Molecul. Biol. (Russ.) 11: 1160, 1977.Google Scholar
  37. 37.
    Okachi, R., Misawa, M., Deguchi, I. & Nara, T. Agr. Biol. Chem. 36: 1193, 1972.CrossRefGoogle Scholar
  38. 38.
    Marconi, W., Bartoli, F., Cecere, F., Galli, G. & Morisi, F. Agr. Biol. Chem. 39: 277, 1975.CrossRefGoogle Scholar
  39. 39.
    Shimizu, M., Masuike, I., Fijita, H., Iida, I., Kimura, K. & Nara, T. Agr. Biol. Chem. 39: 1745, 1975.CrossRefGoogle Scholar
  40. 40.
    Fujii, I., Matsumoto, K. & Watanabe, I. Process Biochem. 11: 21, 1976.Google Scholar
  41. 41.
    Okachi, R. & Nara, T. Agr. Biol. Chem. 37: 2797, 1973.CrossRefGoogle Scholar
  42. 42.
    Shimizu, M., Ocachi, R., Kimura, K. & Nara, T. Agr. Biol. Chem. 39: 1655, 1975.CrossRefGoogle Scholar
  43. 43.
    Svedas, V. K., Klyosov, A. A., Nys, P. S., Savitskaya, Ye. M. & Sinitsin, A. P. In “First National Symposium on Production and Use of Immobilized Enzymes”, Abstracts (Russ.), Tallin, 1974, p. 82.Google Scholar
  44. 44.
    Berezin, I. V., Klibanov, A. M., Klyosov, A. A., Martinek, K. & Svedas, V. K. Febs Lett. 49: 325, 1975.CrossRefGoogle Scholar
  45. 45.
    Nys, P. S., Savitskaya, Ye. M., Klyosov, A. A., Sinitsin, A. P., Svedas, V. K. & Berezin, I. V. Antibiotika (Russ.) 23: 46, 1978.Google Scholar
  46. 46.
    Goldstein, L., Levin, Y. & Katchalski, E. Biochemistry 3: 1913, 1964.CrossRefGoogle Scholar
  47. 47.
    Streltsova, Z. A., Svedas, V. K., Maksimenko, A. V., Klyosov, A. A., Braudo, Ye. Ye., Tolstoguzov, V. B. & Berezin, I. V. Bioorg. Khim. (Russ.) 1: 1464, 1975.Google Scholar

Copyright information

© Plenum Press, New York 1980

Authors and Affiliations

  • V. K. Svedas
    • 1
  • A. L. Margolin
    • 1
  • I. V. Berezin
    • 1
  1. 1.Moscow State UniversityMoscowUSSR

Personalised recommendations