Skip to main content

Microbial metabolites containing nitrogen

  • Chapter
The Biosynthesis of Secondary Metabolites
  • 128 Accesses

Abstract

There is a wide variety of metabolites containing nitrogen, which is produced by micro-organisms. The nitrogen atom (or atoms) most frequently is derived ultimately from an α-amino acid which also provides at least part of the carbon skeleton. Modifications to cyclic dipeptides are commonly encountered as secondary metabolites (Sections 7.3 and 7.4). In the case of the vastly important pharmaceuticals, the penicillins and cephalosporins (Section 7.6.5), a linear tripeptide is involved in biosynthesis.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 39.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 54.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Herbert, R. B. (1980), in Rodd’s Chemistry of Carbon Compounds, 2nd Edn, (ed. S. Coffey), Elsevier, Amsterdam, vol. IV L, pp. 291–455.

    Google Scholar 

  2. Guengerich, F. P., Snyder, J. J. and Broquist, H. P. (1973), Biochemistry, 12, 4264–9.

    Article  Google Scholar 

  3. Bach, M. L. and Gilvarg, C. (1966), J. Biol. Chem., 241, 4563–4.

    Google Scholar 

  4. Kanie, M., Fujimoto, S. and Foster, J. W. (1966), J. Bact., 91, 570–7.

    Google Scholar 

  5. Terashima, T., Idaka, E., Kishi, Y. and Goto, T. (1973), J. Chem. Soc. Chem. Comm., 75–6.

    Google Scholar 

  6. Dobson, T. A., Desaty, D., Brewer, D. and Vining, L. C. (1967), Can. J. Biochem., 45, 809–23.

    Article  Google Scholar 

  7. Helbling, A. M. and Viscontini, M. (1976), Helv. Chim. Acta, 59, 2284–9.

    Article  Google Scholar 

  8. Wright, J. L. C., Vining, L. C., Mclnnes, A. G., Smith, D. G. and Walter, J. A. (1977), Can. J. Biochem., 55, 678–85.

    Google Scholar 

  9. Leete, E., Kowanko, N., Newmark, R. A., Vining, L. C., Mclnnes, A. G. and Wright, J. L. C. (1975), Tetrahedron Lett., 4103–6.

    Google Scholar 

  10. Iwai, Y., Kumano, K. and Omura, S. (1978), Chem. Pharrn. Bull. ( Japan ), 26, 736–9.

    Google Scholar 

  11. Birch, A. J. and Simpson, T. J. (1979), J. Chem. Soc. Perkin I, 816–22.

    Article  Google Scholar 

  12. Vining, L. C. and Wright, J. L. C. (1977), in Biosynthesis (Specialist Periodical Reports) (ed. J. D. Bu’Lock ), The Chemical Society, London, vol. 5, pp. 240–305.

    Google Scholar 

  13. Allen, C. M., jun. (1973), J. Amer. Chem. Soc., 95, 2386–7.

    Article  Google Scholar 

  14. Marchelli, R., Dossena, A. and Casnati, G. (1975), J. Chem. Soc. Chem. Comm., 779–80.

    Google Scholar 

  15. Baldas, J., Birch, A.J. and Russell, R. A. (1974), J. Chem. Soc. Perkin I, 50–2.

    Article  Google Scholar 

  16. MacDonald, J. C. and Slater, G. P. (1975), Can. J. Biochem., 53, 475–8.

    Article  Google Scholar 

  17. Kirby, G. W. and Narayanaswami, S. (1976), J. Chem. Soc. Perkin I, 1564–7.

    Article  Google Scholar 

  18. MacDonald, J. C. (1965), Biochem. J., 96, 533–8.

    Google Scholar 

  19. Akers, H. A., Llinás, M. and Nielands, J. B. (1972), Biochemistry, 11, 2283–91.

    Article  Google Scholar 

  20. Hanke, T. and Diekmann, H. (1974), Arch. Microbiol., 95, 227–36.

    Article  Google Scholar 

  21. Barrow, K. D., Colley, P. W. and Tribe, D. E. (1979), J. Chem. Soc. Chem. Comm., 225–6.

    Google Scholar 

  22. Kirby, G. W., Patrick, G. L. and Robins, D. J. (1978), J. Chem. Soc. Perkin I, 1336–8.

    Article  Google Scholar 

  23. Kirby, G. W. and Varley, M. J. (1974), J. Chem. Soc. Chem. Comm., 833–4.

    Google Scholar 

  24. Aboutabl, El S. A., El Azzouny, A., Winter, K. and Luckner, M. (1976), Phytochemistry, 15, 1925–8.

    Article  Google Scholar 

  25. Chang, C., Floss, H. G., Hurley, L. H. and Zmijewski, M. (1976), J. Org. Chem., 41, 2932–4.

    Article  Google Scholar 

  26. Hurley, L. H., Gairola, C. and Das, N. V. (1976), Biochemistry, 15, 3760–9.

    Article  Google Scholar 

  27. Floss, H. G. (1976), Tetrahedron, 32, 873–912.

    Article  Google Scholar 

  28. Lee, S.-L., Floss, H. G. and Heinstein, P. (1976), Arch. Biochem. Biophys., 177, 84–94.

    Article  Google Scholar 

  29. Plieninger, H., Meyer, E., Maier, W. and Gröger, D. (1978), Annalen, 813–7.

    Google Scholar 

  30. Floss, H. G., Tcheng-Lin, M., Chang, C., Naidoo, B., Blair, G. E., Abou-Chaar, C. I. and Cassady, J. M. (1974), J. Amer. Chem. Soc., 96, 1898–909.

    Article  Google Scholar 

  31. Abe, M. (1970), paper presented at the first International Symposium on Genetics of Industrial Micro-organisms, Prague, (see ref. [27]).

    Google Scholar 

  32. Gröger, D., Mothes, K, Floss, H. G. and Weygand, F. (1963), Z. Naturforsch., 18b, 1123–4.

    Google Scholar 

  33. Gröger, D., Johne, S. and Härtling, S. (1974), Biochem. Physiol. Pflanzen., 166, 33–43.

    Google Scholar 

  34. Floss, H. G., Tcheng-Lin, M., Kobel, H. and Stadler, P. (1974), Experientia, 30, 1369–70.

    Article  Google Scholar 

  35. McGrath, R. M., Stein, P. S., Ferreira, N. P. and Neethling, D. C. (1976), Bio-org. Chem., 5, 11–23.

    Google Scholar 

  36. Mascaro, L., jun., Hörhammer, R., Eisenstein, S., Sellers, L. K., Mascaro, K. and Floss, H. G. (1977), J. Amer. Chem. Soc., 99, 273–4.

    Article  Google Scholar 

  37. Gould, S.J. and Darling, D. S. (1978), Tetrahedron Lett. 3207–10.

    Google Scholar 

  38. Martin, L. L., Chang, C.-J., Floss, H. G., Mabe, J. A., Hagaman, E. W. and Wenkert, E. (1972), J. Amer. Chem. Soc., 94, 8942–4.

    Article  Google Scholar 

  39. Salcher, O., Lingens, F. and Fischer, P. (1978), Tetrahedron Lett., 1978, 3097–100.

    Article  Google Scholar 

  40. Ritter, C. and Luckner, M. (1971), Eur. J. Biochem., 18, 391–400.

    Article  Google Scholar 

  41. Butenandt, A. and Beckmann, R. (1955), Z. Physiol. Chem., 301, 115–7.

    Article  Google Scholar 

  42. Herbert, R. B. (1974), Tetrahedron Lett., 4525–8.

    Google Scholar 

  43. Etherington, T., Herbert, R. B., Holliman, F. G. and Sheridan, J. B. (1979) J. Chem. Soc. Perkin I, 2416–9.

    Google Scholar 

  44. Byng, G. S. and Turner, J. M. (1977), Biochem. J., 164, 133–45.

    Google Scholar 

  45. Herbert, R. B, Holliman, F. G. and Ibberson, P. N. (1972), J. Chem. Soc. Chem. Comm., 355–6.

    Google Scholar 

  46. Flood, M. E., Herbert, R. B. and Holliman, F. G. (1972), J. Chem. Soc. Perkin I, 622–6.

    Article  Google Scholar 

  47. Simonsen, J. N., Paramasigamani, K., Vining, L. C., Mclnnes, A. G., Walter, J. A. and Wright, J. L. C. (1978), Can. J. Microbiol., 24, 136–42.

    Article  Google Scholar 

  48. Hornemann, U., Kehrer, J. P. and Eggert, J. H. (1974), J. Chem. Soc. Chem. Comm., 1045–6.

    Google Scholar 

  49. Haber, A., Johnson, R. D. and Rinehart, K. L., jun. (1977), J. Amer. Chem. Soc., 99, 3541–4.

    Article  Google Scholar 

  50. Milavetz, B., Kakinuma, K., Rinehart, K. L., jun., Rolls, J. P. and Haak, W.J. (1973), J. Amer. Chem. Soc., 95, 5793–5.

    Article  Google Scholar 

  51. Ghisalba, O., Traxler, P. and Nüesch, J. (1978), J. Antibiotics, 31, 1124–31.

    Google Scholar 

  52. White, R.J. and Martinelli, E. (1974), FEBS Lett., 49, 233–6.

    Article  Google Scholar 

  53. Ghisalba, O. and Nüesch, J. (1978), J. Antibiotics, 31, 215–25.

    Google Scholar 

  54. Vederas, J. C. and Tamm, C. (1976), Helv. Chim. Acta, 59, 558–66.

    Article  Google Scholar 

  55. Nadzan, A. M. and Rinehart, K. L., jun. (1976), J. Amer. Chem. Soc., 98, 5012–4.

    Article  Google Scholar 

  56. Wasserman, H. H., Shaw, C. K., Sykes, R.J. and Cushley, R.J. (1974), Tetrahedron Lett., 2787–90.

    Google Scholar 

  57. Gerber, N. N., Mclnnes, A. G., Smith, D. G., Walter, J. A., Wright, J. L. C. and Vining, L. C. (1978), Can. J. Chem., 56, 1155–63.

    Article  Google Scholar 

  58. Hosada, J., Tani, N., Konomi, T., Ohsawa, S., Aoki, H. and Imanaka, H. (1977), Agric. and Biol. Chem. (Japan), 41, 2007–12.

    Article  Google Scholar 

  59. Elson, S. W. and Oliver, R. S. (1978), J. Antibiotics, 31, 586–92.

    Google Scholar 

  60. Flynn, E. H. (ed.) (1972), Cephalosporins and Penicillins, Chemistry and Biology, Academic Press, New York.

    Google Scholar 

  61. Aberhart, D.J. (1977), Tetrahedron, 33, 1545–59.

    Article  Google Scholar 

  62. Booth, H., Bycroft, B. W., Wels, C. M., Corbett, K. and Maloney, A. P. (1976), J. Chem. Soc. Chem. Comm., 110–1.

    Google Scholar 

  63. Huddleston, J. A., Abraham, E. P., Young, D. W., Morecombe, D. J. and Sen, P. K. (1978), Biochem.J., 169, 705–7.

    Google Scholar 

  64. Neuss, N., Nash, C. H., Lemke, P. A. and Grutzner, J. B. (1971), J. Amer. Chem. Soc., 93, 2337–9.

    Article  Google Scholar 

  65. Neuss, N., Nash, C. H., Lemke, P. A. and Grutzner, J. B. (1971), Proc. Roy. Soc., B179, 335–44.

    Google Scholar 

  66. Kluender, H., Huang, F.-C., Fritzberg, A., Schnoes, H., Sih, C. J., Fawcett, P. and Abraham, E. P. (1974), J. Amer. Chem. Soc., 96, 4054–5.

    Article  Google Scholar 

  67. Aberhart, D. J., Chu, J. Y.-R., Neuss, N, Nash, C. H, Occolowitz, J., Huckstep, L. L. and De La Higura, N. (1974), J. Chem. Soc. Chem. Comm., 564–5.

    Google Scholar 

  68. Fawcett, P. A., Usher, J. J., Huddleston, J. A., Bleaney, R. C., Nisbet, J.J. and Abraham, E. P. (1976), Biochem.J., 157, 651–60.

    Google Scholar 

  69. Khosata, M. and Demain, A. L. (1976), Biochem. Biophys. Res. Comm., 70, 465–73.

    Article  Google Scholar 

  70. Scott, A. I., Yoo, S. E., Chung, S.-K. and Lacadie, J. A. (1976), Tetrahedron Lett. 1137–40.

    Google Scholar 

  71. Cheney, J., Moores, C. J., Raleigh, J. A., Scott, A. I. and Young, D. W. (1974), J. Chem. Soc. Chem. Comm., 47–8.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

Copyright information

© 1981 R. B. Herbert

About this chapter

Cite this chapter

Herbert, R.B. (1981). Microbial metabolites containing nitrogen. In: The Biosynthesis of Secondary Metabolites. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-5833-3_7

Download citation

  • DOI: https://doi.org/10.1007/978-94-009-5833-3_7

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-009-5835-7

  • Online ISBN: 978-94-009-5833-3

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics