Skip to main content

Abstract

Speculations regarding the biogenesis of natural products, particularly those of plant origin, have excited the interest of organic chemists for more than fifty years, and several basic ideas have persisted in spite of the technical impossibility of putting them to experimental test. The use of biochemical techniques involving labelled atoms, coupled with various other developments such as microchemistry and chromatography have now served to provide verification of some of these earlier ideas. The hypothesis that many complex natural products, including aromatic compounds, were built up from acetyl units was advanced by Collie in 19071) and, as a result of modern biochemical research is now known to be essentially correct. The well-known isoprene rule as a basis for terpenoid structure has also now been provided with solid biochemical backing. Similarly, the early ideas on amino-acids as precursors of alkaloids date back to a paper by Robinson in 19172). A more recent biogenetic hypothesis is based upon the growing realisation that free radical reactions play an important part in biochemical processes, and this has led to some novel biogenetic ideas which will be referred to. With the advent of the antibiotics, the range of available natural products has increased enormously both in number and type.

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. J. N. Collie, J. Chem. Soc. 91, 1806 (1907).

    Article  Google Scholar 

  2. R. Robinson, J. Chem. Soc. Ill, 876 (1917).

    Google Scholar 

  3. F. Lipmann, Proc. Nat. Acad. Sci. 44, 67 (1958); P. Berg and E. J. Offengand, ibid., p. 78.

    Article  Google Scholar 

  4. B. D. Davis, Biosynthesis of the Aromatic Amino Acids, Chapter Via in: A Symposium on Amino Acid Metabolism, ed. by W. D. McElroy and H. B. Glass, ( The Johns Hopkins Press, Baltimore 1955 ).

    Google Scholar 

  5. P. Lynen, Nature 174, 962 (1954).

    Article  Google Scholar 

  6. P. Lepmann, Science 120, 855 (1954).

    Article  Google Scholar 

  7. J. V. Formica and R. O. Brady, J. Amer. Chem. Soc. 81 752 (1959).

    Article  Google Scholar 

  8. S. J. Wakil, J. Amer. Chem. Soc. 80, 6465 (1958).

    Article  Google Scholar 

  9. Various authors: Biosynthesis of Terpenes and Sterols, Ciba Foundation Symposium, London, ed. by G. E. W. Wolstenholme and M. O’connor (London 1959 ).

    Google Scholar 

  10. F. Lynen, H. Eggerer, U. Henning and I. Kessel, Angew. Chem. 70, 738 (1958).

    Article  Google Scholar 

  11. J. W. Ogilvie jr. and R. G. Langdon, J. Amer. Chem. Soc. 81, 754 (1959); J. W. Ogilvie jr., ibid., p. 756.

    Google Scholar 

  12. D. H. R. Barton and T. Cohen, Some Biogenetic Aspects of Phenol Oxidation, in: Festschrift A. Stoll (Basel 1955 ), p. 117.

    Google Scholar 

  13. A. I. Scott, Proc. Chem. Soc. 1959, 195.

    Google Scholar 

  14. F. Bohlmann, Angew. Chem. 67, 389 (1955).

    Article  Google Scholar 

  15. M. Anchel, Trans. N. Y. Acad. Sci. 16, 337 (1954).

    Google Scholar 

  16. J. D. Bu’lock and H. Gregory, Biochem. J. 72, 322 (1959).

    Google Scholar 

  17. J. Gripenberg, Acta Chem. Scand. 6, 580 (1952).

    Article  Google Scholar 

  18. A. J. Birch and F. W. Donovan, Austr. J. Chem. 6, 360 (1953).

    Article  Google Scholar 

  19. A. J. Birch, Biosynthetic Theories in Organic Chemistry, in: Perspectives in Organic Chemistry ( vol. ded. to Sir R. Robinson ), ed. by Sir A. R. Todd, Interscience Publishers, Inc., New York and London, (1956), p. 134.

    Google Scholar 

  20. A. J. Birch, R. A. Massy-Westropp and C. J. Moye, Chem. and Ind. 1955, 683.

    Google Scholar 

  21. A. J. Birch, R. A. Massy-Westropp, R. W. Rickards and H. Smith, J. Chem. Soc. 1958, 360.

    Google Scholar 

  22. A. J. Birch, P. Fitton, E. Pride, A. J. Ryan, H. Smith and W. B. Whalley, J. Chem. Soc. 1958, 4576.

    Google Scholar 

  23. J. MacMillan, J. Chem. Soc. 1954, 2585.

    Google Scholar 

  24. A. J. Birch, G. E. Blance and H. Smith, J. Chem. Soc. 1958, 4582.

    Google Scholar 

  25. F. W. Bassett and S. W. Tanenbaijm, Exper. 14, 38 (1958).

    Article  Google Scholar 

  26. A. J. Birch and R. A. Massy-Westropp, J. Chem. Soc. 1957, 2215.

    Google Scholar 

  27. H. Brockmann and B. France:, Ber. dtseh. chem. Ges. 88, 1792 (1955).

    Google Scholar 

  28. R. B. Woodward, Angew. Chem. 69, 50 (1957); The Structure and Biogenesis of the Maerolides, a new Class of Natural Products, in: Festschrift A. Stoll (Basel 1957 ), p. 524.

    Article  Google Scholar 

  29. P. P. Wiley, K. Gerzon, E. H. Flynn, M. V. Sigal jr., O. Weaver, U. C. Quarck, R. R. Chauvette and R. Monahan, J. Am. Chem. Soc. 79, 6062 (1957).

    Article  Google Scholar 

  30. C. Djerassi and J. A. Zderic, J. Amer. Chem. Soc. 78, 6390 (1956).

    Article  Google Scholar 

  31. C. Djerassi and O. Halpern, J. Amer. ehem. Soc. 79, 2022 (1957); Tetrahedron 3, 255 (1958).

    Article  Google Scholar 

  32. H. Brockmann, Angew. Chem. 69, 237 (1957).

    Google Scholar 

  33. R. Anliker and K. Gubler, Helv. Chim. Acta 40, 119 (1957).

    Article  Google Scholar 

  34. J. B. Patrick, R. B. Williams and J.S. Webb, J. Amer. chem. Soc. 80, 6689 (1958).

    Article  Google Scholar 

  35. J. R. D. McCormick, N. O. Sjolander, U. Hirsch, E. R. Jensen and A. P. Doer- Schuk, J. Amer. chem. Soc. 79, 4561 (1957).

    Article  Google Scholar 

  36. J. R. D. McCormick, PH. A. Miller, J. A. Growich, N. O. Sjolander and A. P. Doerschuk, J. Amer. chem. Soc. 80, 5572 (1958).

    Article  Google Scholar 

  37. American Cyanamide Co. Austral. Patents 35376–7/57.

    Google Scholar 

  38. R. B. Woodward, Angew. Chem. 68, 13 (1956).

    Article  Google Scholar 

  39. R. Robinson, The Structural Relations of Natural Products ( Clarendon Press, Oxford 1955 ).

    Google Scholar 

  40. A. J. Birch (private communication).

    Google Scholar 

  41. A. J. Birch, R. J. English, R. A. Massy-Westropp, M. Slaytor and H. Smith, J. Chem. Soc. 1958, 365; A. J. Birch, R. J. English, R. A. Massy-Westropp and H. Smith, ibid., p. 369.

    Google Scholar 

  42. R. K. Callow, Chem. Soc. Ann. Rep. 1956, 307; P. Bladon, ibid. 1957, 275.

    Google Scholar 

  43. H. S. Burton, E. P. Abraham and H. M. E. Cardwell, Bioehem. J. 62, 171 (1956).

    Google Scholar 

  44. N. J. Cartwright, Biochem. J. 60, 238 (1955).

    Google Scholar 

  45. S. A. Fusabi, R. P. Frohardt, A. Ryder, TH. H. Haskell, D. W. Johannessen, C. C. Elder and Q. R. Bartz, J. Am. Chem. Soc. 76, 2878 (1954); S. A. Fusabi, TH. H. Haskell, R. P. Frohardt and Q.R. Bartz, ibid. p. 2881.

    Google Scholar 

  46. L. Pons and H. Veldstra, Rec. Tray. Chim. 74, 1217 (1955).

    Article  Google Scholar 

  47. H. W. Dion, S. A. Fusari, Z. L. Jakubowski, J. G. Zora and Q. R. Bartz, J. Amer. chem. Soc. 78, 3075 (1956).

    Article  Google Scholar 

  48. F. A. Kuehl jr., F. J. Wolf, N. R. Tbenneb, R. L. Peck, E. Howe, B. D. Hunne- Well, G. Downing, E. Newstead, K. Folkers, R. P. Buhs, I. Putter, R. Ormond, J. E. Lyons and L. Chaiet, J. Amer. chem. Soc. 77, 2344 (1955).

    Google Scholar 

  49. G-. A. Snow, J. chem. Soc. 1954, 4080.

    Google Scholar 

  50. W. B. Sutton and L. Stanfield, Antibiotics and Chemotherapy 5, 582 (1955).

    Google Scholar 

  51. L. Ettlinger, E. Gaumann, R. Hutter, W. Keller-Schierlein, F. Kradolfer, L. Neipp, V. Prelog and H. Zahner, Helv. Chim. Acta 42, 563 (1959).

    Article  Google Scholar 

  52. J. T. Edward, Ann. Rep. Chem. Soc. 51, 247 (1954).

    Google Scholar 

  53. D. W. Woolley, G. Schaitner and A. C. Brattn, J. Biol. Chem. 215, 485 (1955).

    Google Scholar 

  54. P. Fryth, C. W. Waller, B. L. Hutchings and J. H. Williams, J. Amer, chem. Soc. 80, 2736 (1958).

    Article  Google Scholar 

  55. B. R. Baker, J. P. Joseph and J. H. Williams, J. Amer. ehem. Soc. 77, 1 (1955).

    Article  Google Scholar 

  56. G. M. Tener, E. Van Tamelen and F. M. Strong, Fed. Proc. 12, 280 (1953).

    Google Scholar 

  57. P. Brookes, A. T. Fuller and J. Walker, J. Chem. Soc. 1957, 689.

    Google Scholar 

  58. H. E. V. Arnstein and P. T. Grant, Baet. Rev. 20, 133 (1956).

    Google Scholar 

  59. H. R. V. Arnstein, Ann. Rep. Chem. Soc. 54, 339 (1957).

    Google Scholar 

  60. F. R. Batchelor, F. P. Doyle, J. H. C. Nayler and G. N. Rolinson, Nature 183, 257 (1959).

    Article  Google Scholar 

  61. E. P. Abraham, G. G. F. Newton and C. W. Hale, Bioehem. J. 58, 94 (1954).

    Google Scholar 

  62. G. G. P. Newton and E. P. Abraham, Nature 175, 548 (1955).

    Article  Google Scholar 

  63. G. Dunn, J. J. Gallagher, G. T. Newbold and F. S. Spring, J. chem. Soc. 1959, SuppL 126; G. Dunn, G. T. Newbold and F. S. Spring, ibid., Suppl. 131.

    Google Scholar 

  64. A. J. Birch, R. A. Massy-Westropp and R. W. Rickards, Chem. and Ind. 1955, 1599.

    Google Scholar 

  65. M. R. Bell, J. R. Johnson, B. S. Wildi and R. B. Woodward, J. Amer. chem. Soc. 80, 1001 (1958).

    Article  Google Scholar 

  66. PL. A. Plattner and U. Nager, Helv. Chim. Acta 31, 2192 (1948).

    Article  Google Scholar 

  67. A. H. Cook, S. F. Cox and T. H. Farmer, Nature 162, 61 (1948).

    Article  Google Scholar 

  68. PL. A. Plattner, N. Clattson-Kaas, A. Boller and U. Nager, Helv. Chim. Acta 31, 860 (1948).

    Article  Google Scholar 

  69. TH. H. Haskell, S. A. Fitsari, R. P. Frohardt and Q. R. Bartz, J. Artier, chem. Soc. 74, 599 (1952).

    Article  Google Scholar 

  70. H. E. Carter, R. K. Clark jr., P. Koim, J. W. Rothrock, W. R. Taylor, C. A. West, G. B. Whitfield and W. G. Jackson, J. Amer. chem. Soc. 76, 566 (1954).

    Google Scholar 

  71. K. Nakaniski, T. Ito and Y. Hirata, J. Amer. chem. Soc. 76, 2845 (1954).

    Article  Google Scholar 

  72. D. E. Ames, R. E. Bowman, J. F. Cavalla and D. D. Evans, J. chem. Soc. 1955, 4260; D. E. Ames and R. E. Bowman, ibid., p. 4264.

    Google Scholar 

  73. W. A. Sexton, Chemical Constitution and Biobgical Activity, 2nd Edn. (Spon, London, 1953); German Edn.: Chemische Konstitution und biologische Wirkung, ( Verlag Chemie, Weinheim 1958 ), p. 193.

    Google Scholar 

  74. R. Schwyzer and P. Sieber, Helv. Chim. Acta 40, 624 (1957).

    Article  Google Scholar 

  75. R. Schwyzer and P. Sieber, Helv. Chim. Acta 41, 1582 (1958).

    Article  Google Scholar 

  76. E. Katchalski, A. Berger, L. Bichowsky-Slomnicki and J. Kurte, Nature 176, 118 (1955).

    Article  Google Scholar 

  77. A. Paladini and L. C. Craig, J. Amer. ehem. Soc. 76, 688 (1954).

    Article  Google Scholar 

  78. G. Biserte and M. Dautrevaux, Bull. Soc. Chim. Biol. 39, 795 (1957).

    Google Scholar 

  79. W. Hausmahn and L. C. Craig, J. Biol. Chem. 198, 405 (1952).

    Google Scholar 

  80. TH. Wieland and W. Schön, Lieb. Ann. Chem. 593, 157 (1955).

    Article  Google Scholar 

  81. G. G. F. Newton and E. P. Abraham, Biochem. J. 53, 597 (1953).

    Google Scholar 

  82. I. M. Lockhabt, E. P. Abrahm and G. G. F. Newton, Biochem. J. 61, 534 (1955).

    Google Scholar 

  83. G. G. F. Newton, E. P. Abraham and N. K. Berridge, Nature 171, 606 (1953).

    Article  Google Scholar 

  84. G. Alderton, J. Amer. ehem. Soc. 75, 2391 (1953).

    Article  Google Scholar 

  85. A. Stracher and L. C. Craig, J. Amer. ehem. Soc. 81, 696 (1959).

    Article  Google Scholar 

  86. H. Brockmann and H. Geeren, Lieb. Ann. Chem. 603, 216 (1957).

    Article  Google Scholar 

  87. L. C. Vining and W. A. Taber, Canad. J. Chem. 35, 1109 (1957).

    Article  Google Scholar 

  88. J. C. Sheehan, H. G. Zachau and W. B. Lawson, J. Amer. Chem. Soc. 80, 3349 (1958).

    Article  Google Scholar 

  89. R. B. Arnold, A. W. Johnson and A. B. Mauger, J. chem. Soc. 1958, 4466.

    Google Scholar 

  90. W. Keller-Schierlein, M. LJ. Mihailovic and V. Prelog, Helv. Chim. Acta 42, 305 (1959).

    Article  Google Scholar 

  91. H. Brockmann and H. Muxeeldt, Chem. Ber. 91, 1242 (1958).

    Article  Google Scholar 

  92. A. Butenandt, Angew. Chem. 69, 16 (1957).

    Article  Google Scholar 

  93. C. B. Thorne, C. G. Gomez and R. D. Housewright, J. Bact. 69, 357 (1955i); C. B. Thorne and D. M. Molnar, ibid. 70, 420 (1955n).

    Article  Google Scholar 

  94. S. Blackburn, W. R. Middlebrook and H. Phillips, Nature 150, 57 (1942).

    Article  Google Scholar 

  95. P. Desntjelle and A. Casal, Bioehim. Biophys. Acta 2, 64 (1948).

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1960 Birkhäuser Verlag Basel

About this chapter

Cite this chapter

Sexton, W.A. (1960). The Structure and Biogenesis of Certain Antibiotics. In: Jucker, E. (eds) Fortschritte der Arzneimittelforschung / Progress in Drug Research / Progrès des recherches pharmaceutiques. Fortschritte der Arzneimittelforschung / Progress in Drug Research / Progrès des Recherches Pharmaceutiques, vol 2. Birkhäuser Basel. https://doi.org/10.1007/978-3-0348-7038-2_9

Download citation

  • DOI: https://doi.org/10.1007/978-3-0348-7038-2_9

  • Publisher Name: Birkhäuser Basel

  • Print ISBN: 978-3-0348-7040-5

  • Online ISBN: 978-3-0348-7038-2

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics