The inhibitory mechanisms of glucose and carbon dioxide on the biosyntheses of penicillins and cephalosporins

Journal of Biotechnology

Volumn 51, Issue 2, 1996, Pages 137-148

  Yang, Zhi Fa ^a   Schügerl, Karl ^a   Lucas, Luz ^a  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

Author keywords

Bound 6 APA; Carbon dioxide inhibition; Cephalosporins; Glucose inhibition; Lact ose inhibition; Penicillins

Indexed keywords

ANTIBIOTICS; CARBON DIOXIDE; ENZYME INHIBITION; ENZYME KINETICS; GLUCOSE; ORGANIC ACIDS; REACTION KINETICS;

AMINOPENICILLANIC ACID (APA); CEPHALOSPORINS; LACTOSE INHIBITION; PENICILLINS;

BIOSYNTHESIS;

6 AMINOPENICILLANIC ACID; CARBON DIOXIDE; CEPHALOSPORIN; GLUCOSE; LACTOSE; PENICILLIN G;

ANTIBIOTIC BIOSYNTHESIS; ARTICLE; HYPOTHESIS; NONHUMAN; PRIORITY JOURNAL;

EID: 0030298464     PISSN: 01681656     EISSN: None     Source Type: Journal    
DOI: 10.1016/0168-1656(96)01592-1     Document Type: Article

References (71)

1. Aberhart, D.J. (1977) Biosynthesis of β-lactam antibiotics. Tetrahedron 33, 1545-1559.
2. Abraham, E.P. (1974) Biosynthesis and Enzymic Hydrolysis of Penicillins and Cephalosporins, University of Tokyo Press, Tokyo.
3. Abraham, E.P. (1986) Enzymes involved in penicillin and cephalosporin formation. In: Kleinkauf, H., Dohren, H., Dornauer, H. and Nesemann, G. (Eds.), Regulation of Secondary Metabolite Formation, VCH Verlag, Weinheim, pp. 115.
4. Balasingham, K., Warburton, D., Dunnill, P. and Lilly, M.D. (1972) 'The isolation and kinetics of penicillin amidase from Escherichia coli'. Biochim. Biophys. Acta 276, 250-256.
5. Baldwin, J.E., Adlington, R.M., Crabbe, M.J., Knight, G., Nomoto, T., Schofield, C.J. and Ting, H.-H.(1987) The enzymatic ring expansion of penicillins to cephalosporins: side chain specificity. Tetrahedron 43(13), 3009-3014.
6. Baldwin, J.E. and Abraham, E.P. (1988) The biosynthesis of penicillins and cephalosporins. Natural Product Report, 129-145.
7. Ballio, A. Chain, E.B., Dentice, Di Accadia, F., Mauri, M., Rauer, K., Schlesinger, M.J. and Schlesinger, S. (1961) Identification of a Compound related to 6-Aminopenicillanic acid, isolated from Culture Media of Penicillium chrysogenum. Nature 191, 909-910.
8. Batchelor, F.R., Chain, E.B. and Rolinson, G.N. (1961a) 6-Aminopenicillanic acid I. Proc. Roy. Soc. (London), Ser. B 154, 478-489.
9. Batchelor, F.R., Doyler, F.P., Nayler, J.H.C. and Rolinson, G.N. (1959) Synthesis of Penicillin: 6-Aminopenicillanic Acid in Penicillin Fermentations. Nature 183(4656), 257-258.
10. Batchelor, F.R., Gazzard, D. and Nayler, J.H.C. (1961b) Action of Carbon Dioxide on 6-Aminopenicillanic Acid. Nature 191, 910-911.
11. Batchelor, F.R., Cole, M., Gazzard, D. and Rolinson, G.N. (1962) Penicillin-like substances in preparations of 6-amino penicillanic acid, Nature 195, 954-955.
12. Bayer, T., Zhou, W., Holzhauer, K. and Schügerl, K. (1989) Investigations of cephalosporin C production in an airlift tower loop reactor. Appl. Microbiol. Biotechnol. 30, 26-33.
13. Biryukov, V.V. and Kantere, V.M. (1982) Optimization of secondary metabolite production using on-line real-time computer. In: Krumphanzl, V., Sikyta, B. and Vanek, Z. (Eds.), Overproduction of Microbial Products, Academic, New York, pp. 687-701.
14. Cole, M. (1966) Microbial Synthesis of Penicillins, Part 1 and Part 2. Process Biochem. 9, 334-338; 10, 373-377.
15. Cole, M. (1969a) Hydrolysis of penicillins and related compounds by the cell-bound penicillin acylase of Esherichia coli. Biochem. J. 115, 733-739.
16. Cole, M. (1969b) Deacylation of acylamino compounds other than penicillins by the cell-bound penicillin acylase of E. coli. Biochem. J. 115, 741-745.
17. Cole, M. (1969c) Penicillins and other acylamino compounds synthesized by the cell-bound penicillin acylase of E. coli. Biochem. J. 115, 747-756.
18. Cole, M. (1969d) Factors affecting the synthesis of ampicillin and hydroxypenicillins by the cell-bound penicillin acylase of E. coli. Biochem. J. 115, 757-764.
19. Fawcett, P.A., Usher, J.J. and Abraham, E.P. (1975) Behavior of tritrium-labeled isopenicillin N and 6-penicillanic acid as potential penicillin precursors in an extract of Penicillium chrysogenum. Biochem. J. 151, 741-746.
20. de Flines, J. (1980) Biotechnology-Its past, present and future. In: A. Verbraeck (Ed.), Biotechnology a Hidden Past, a Shining Future. 13th International TNO Conference, Rotterdam, The Netherlands. Netherlands Central Organization for Applied Scientific Research TNO, The Hague, pp. 12-17.
21. Flynn, E.H., McCormick, M.H., Stamper, M.C., De Valeria, H. and Godzeski, C. W. (1962) A new natural penicillin from Penicillium chrysogenum, J. Am. Chem. Soc. 84, 4594-4595.
22. Foster, J.W. (1949) Chemical Activities of Fungi, Academic, New York, pp. 587-593.
23. Grant, N.H., Clark, D.E. and Alburn, H.E. (1962) Poly-6-aminopenicillanic acid. J. Am. Chem. Soc. 84, 876-877.
24. Heim, J., Shen, Y.-Q. Wolfe, S. and Demain, A.L. (1984) Regulation of isopenicillin N synthetase and deacetoxy-cephalosporin C synthetase by carbon source during the fermentation of Cephalosporium acremonium. Appl. Microbiol. Biotechnol. 19, 232-236.
25. Hersbach, G.J.M., Van Der Beek, C.P. and Van Dijck, P.W.M., (1984) The Penicillins: Properties, Biosynthesis, and Fermentation, In: Vandamme, E.J. (Ed.), Biotechnology of Antibiotics, Marcel Dekker, New York, pp. 45-140.
26. Ishimura, F. and Suga, K.-I. (1992) Hydrolysis of penicillin g by combination of immiobilized penicillin acylase and electrodialysis. Biotechnol. Bioengineering 39(2), 171-175.
27. Jarvis, G.F. and Johnson, M.J. (1947) The role of the constituents of synthetic media for penicillin production, J. Am. Chem. Soc. 69, 3010-3017.
28. Jensen, E.B., Nielsen, R. and Emborg, C. (1981) The influence of acetic acid on penicillin production. Eur. J. Appl, Microbiol. Biotechnol. 13, 29-33.
29. Johnson, D.A. and Hardcastle, G.A. (1961) Reaction of 6-amino penicillanic acid with carbon dioxide, J. Am. Chem. Soc. 83, 3534-3535.
30. Kitano, K., Kintaka, K., Katamoto, K., Nara, K. and Nakao, Y. (1975) Occurence of 6-aminopenicillanic acid in culture broths of strains belonging to the genera Thermoascus gymnoascus, Polypaecilum and Malbranchea. J. Ferment. Technol. 53(6) 339-346.
31. Konomi, T., Herchen, S., Baldwin, J.E., Yoshida, M., Hunt, N.A. and Demain, A.L. (1979) Cell-free conversion of d-(L-α-aminoadipyl)-L-cysteinyl-D-valine into an antibiotic with the properties of isopenicillin N in Cephalosporium acremonium. Biochem. J. 184, 427-430.
32. Küenzi, M.T. (1980) Regulation of cephalosporin synthesis in C. acremonium by phosphate and glucose. Arch. Microbiol. 128, 78.
33. Lagerlöf, E., Nathorst-Westfelt, L., Ekström, B. and Sjöberg, B. (1976) Production of 6-aminopenicillanic acid with immobilized Escherichia coli acylase. In: Mosbach, K. (Ed.), Methods in Enzymology, Academic, New York, Vol. 44, pp. 759-768.
34. Lebrihi, A., Lefebvre, G. and Germain, P. (1988) Carbon catabolite regulation of cephamycin C and expandase biosynthesis in Streptomyces clavuligerus. Appl. Microb. Biotechnol. 28, 44-51.
35. Lopez-Nieto, M.J., Revilla, G. and Martin, J.F. (1982) Biosynthesis of the tripeptide D-(L-α-aminoadipyl) L-cysteinyl-D-valine in Penicillium chrysogenum and its control by glucose. In: Ikeda, Y. and Beppu, T. (Eds.), 4th International Symposium on the Genetics of Industrial Microorganisms, Kyoto, Japan, pp. 111.
36. Lurie, L.M., Stepanova, N.E., Bartoshevich, Yu.E. and Levitov, M.M. (1979) Study on physiological role of oils in penicillin biosynthesis, Antibiotiki, Moscow, 24, pp. 86-92.
37. 14C. J. Biol. Chem. 203, 239-250.
38. Martin, J.F. and Liras, P. (1989) Enzymes involved in penicillin, cephalosporin and cephamycin biosynthesis. Adv. Biochem. Eng./Biotechnol. 39, 153-187.
39. Matelova, V. (1981) Less customary raw materials for the production of penicillin. Kvasny Prum. 27, 21-22.
40. Möller, J., Niehoff, J., Hiddessen, R. and K. Schügerl (1992) Influence of medium composition on penicillin V production in a stirred tank reactor. J. Biotechnol. 25, 245-259.
41. Moss, M.O. (1964) Reaction of 6-aminopenicillanic acid with frequentin. Experientia 20, 605.
42. Moss, M.O. and Cole, M. (1964) Reaction of 6-APA with carbohydrates and related substances. Biochem. J. 92, 643-648.
43. Norregaard, P., Holm, H. and Emborg, C. (1984) Organic acids and penicillin production. Appl. Microbiol. Biotechnol, 20, 221-224.
44. 2 on the germination of Penicillium chrysogenum spores. Z. Allg. Mikrobiol. 7, 107-111.
45. 2 on penicillin formation in automatically aerated liquid cultures. Biothchnol. Bioeng, 7, 343-354.
46. O'Sullivan, J. and Abraham, E.P. (1981) Biosynthesis of β-lactam antibiotics. In: Corcoran, J.W. (Ed.), Antibiotics, Springer Verlag, Berlin, Vol. IV, pp. 101-122.
47. 3H]-valine into isopenicillin N. Biochem. J. 184, 421-426.
48. Ott, J.L., Godzeski, C.W., Pavey, D., Farran, J.D. and Horton, D.R. (1962) Biosynthesis of Cephalosporins C: I. Factors Affecting the Fermentation. Appl. Microbiol. 10, 515-523.
49. Pan, S.C., Bonanno, S. and Wagman, G.H. (1959) Efficient utilization of fatty oils as energy source in penicillin fermentation. Appl. Microbiol. 7, 176-180.
50. Queener, S. and Neuss, N. (1982) The biosynthesis of β-lactam antibiotics. In: Morin, R.B. and Gorman, M. (Eds.), The Chemistry and Biology of β-Lactam Antibiotics. Academic, New York, Vol. 3, pp. 1-810.
51. Revilla, G., Luengo, J.M., Villanueva, J.R. and Martin, J.F. (1982) Carbon catabolite repression of penicillin biosynthesis. In: Moo-Young, M. (Ed.), Advances in Biotechnology, Pergamon, New York, Vol. 3, pp. 155-160.
52. Roels, J.A. (1982) Kinetic models in bioengineering. Applications, Prospects and Problems. 3rd International Conference on Computer Application in Fermentation Technology, Manchester, England, 1981, pp. 37-46.
53. Roels, J.A. and Kossen, N.W.F. (1978) On the modeling of microbial metabolism. In: Bull, M.J. (Ed.), Progress in Industrial Microbiology, Elsevier, Amsterdam, Vol. 14, pp. 95-203.
54. Rollins, M.J., Jensen, S.E., Wolfe, S. and Westlake, D.W.S. (1988) Dissolved oxygen control of a maltose feed to batch fermentation of Streptomyces clavuligerus: Effect on cephamycin biosynthesis. Biotechnol. Lett. 10, 295-300.
55. Scheidegger, A., Kuenzi, M.T., Fiechter, A. and Nuesch, J. (1988) Effect of glucose and oxygen on β-lactam biosynthesis by Cephalosporium acremonium. J. Biotechnol. 7, 131.
56. Shewale J.G., Kumar K.K. and Ambekar, G.R. (1987) Evaluation of determination of 6-Aminopenicillanic acid by p-Dimethylaminobenzaldehyde. Biotechnol. Techniques 1(1), 69-72.
57. Smith, A. (1985) Cephalosporins. In: Moo-Young, M. (Ed.), Comprehensive Biotechnology, Pergamon Press, Oxford, England, Vol. 3, pp. 163-185.
58. Soltero, F.V. and Johnson, M.J. (1953) Effect of carbohydrate nutrition on penicillin prodution by P. chrysogenum Q-176. Appl. Microbiol. 1, 52-57.
59. Soltero, F.V. and Johson, M.J. (1954) Continuous Addition of Glucose for Evaluation of Penicillin-Producing Cultures. Appl. Microbiol. 2, 41-44.
60. Squibb and Sons (1979) US Patent No. 4164445.
61. Swartz, R. W. (1979) The use of economic analysis of penicillin G manufacturing costs in establishing priorities for fermentation process improvement. In: Perlman, D. and Tsao, G.T. (Eds.), Annual Reports on Fermentation Processes, Academic, New York, Vol. 3, pp. 75-110.
62. Szarka, L.J., Cino, P.M. and Ko, R.Y. (1992) Penicillin Fermentation Using Hydrocarbons. Process Biochemistry 27, 77-82.
63. Tan, I.K.-P. and Ho, C.-C. (1991) Growth and the production of penicillins in P. chrysogenum with palm oil and its various fractions as carbon sources. Appl. Microbiol. Biotechnol. 36, 163-166.
64. Tome, J., Zook, H.D., Wagner, R.B. and Stone, R.W. (1953) Degradation of radio-active penicillin G. J. Biol. Chem. 203, 251-255.
65. van Suijdam, J.C. and Metz, B. (1981) Influence of engineering variables upon the morphology of filamentous molds. Biotechnol, Bioeng. 23, 111-148.
66. Vicik, S.M., Fedor, A.J. and Swartz, R.W., (1990) Defining an optimal carbon source/methionine feed strategy for growth and cephalosporin C formation by Cephalosporium acremonium. Biotechnol. Prog. 6, 333-340.
67. Vining, L.C., Shapiro, S., Madduri, K. and Stuttard, C. (1990) Biosynthesis and control of β-lactam antibiotics: the early steps in the classical tripeptide pathway. Biotech. Adv. 8, 159-183.
68. Wolff, E.C. and Arnstein, H.R.V. (1960) The metabolism of 6-APA and related compounds by P. chrysogenum and its possible significance for penicillin biosynthesis. Biochem. J. 76, 375-381.
69. Zhang, J.Y. and Demain, A.L. (1991) Regulation of ACV synthetase in penicillin-and cephalosporin-producing microorganisms, Biotech. Adv. 9, 623-641.
70. Zhang, J.Y., Wolfe, S. and Demain, A.L. (1989) Carbon source regulation of the ACV synthetase in Cephalosporium acremonium C-10. Curr. Microbiol. 18, 361-367.
71. Zhou, W.C., Holzhauer-Rieger Dors, K. M. and Schügerl, K. (1992) Influence of medium composition on the cephalosporin C production with a highly productive strain Cephalosporium acremonium. J. Biotechnol. 23, 315-329.