Skip to main content

The Biosynthesis of Rubber

  • Chapter

Part of the book series: Fortschritte Der Chemie Organischer Naturstoffe ((FORTCHEMIE (closed),volume 21))

Zusammenfassung

Of the major biosynthetic pathways of the plant, that associated with the synthesis of rubber has been among the last to be elucidated. All that we know today concerning isoprenoid biogenesis is information acquired since 1949, much of it since 1956. Today, however, rubber biosynthesis may be considered as a problem solved. We can plot out in intimate detail the complete pathway by which carbon atoms present in common plant metabolites such as carbohydrates are converted to the polyisoprene molecule.

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

Buying options

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   44.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   59.99
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

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literaturverzeichnis

  1. Agranoff, B. W., H. Eggerer, U. Henning and F. Lynen: Biosynthesis of Terpenes. VII. Isopentenyl Pyrophosphate Isomerass. J. Biol. Chem. 235, 326 (1960).

    CAS  Google Scholar 

  2. Amdur, B. H., H. Rilling and K. Bloch: Enzymatic Conversion of Mevalonic Acid to Squalene. J. Amer. Chem. Soc. 79, 2646 (1957).

    Article  CAS  Google Scholar 

  3. Archer, B. L.,G. Ayrey, E. G. Cockbain and G. P. Mcsweeney: Incorporation of [I-C14]-Isopentenyl Pyrophosphate into Polyisoprene. Nature 189, 663(1961).

    Article  CAS  Google Scholar 

  4. Arreguin, B., J. Bonner and B. J. Wood: Studies on the Mechanism of Rubber Formation in the Guayule. III. Experiments with Isotopic Carbon. Arch. Biochem. Biophys. 31, 234 (1951).

    Article  CAS  Google Scholar 

  5. Asahina, Y.: Notiz über Seneciosäure. Arch. Pharm. 251, 355 (1913).

    Article  Google Scholar 

  6. Bachhawat, B. K., W. G. Robinson and M. J. Coon: CO2 Fixation in Heart Extracts by β-Hydroxy-Isovaleryl Coenzyme A. J. Amer. Chem. Soc. 76, 3098 (1954).

    Article  CAS  Google Scholar 

  7. Bandurski, R., T. Coyle and J. Bonner: Studies on the Mechanism of Rubber Biosynthesis. Biology 1953, Calif. Inst. of Tech., pp. 118/119.

    Google Scholar 

  8. Beinert, H., D. E. Green, P. Hele, H. Hift, R. W. VON Korff and C. V. Ramakrishnan: The Acetate Activating Enzyme System of Heart Muscle. J. Biol. Chem. 203, 35 (1953).

    CAS  Google Scholar 

  9. Bloch, K.: The Biological Synthesis of Cholesterol. Recent Progr. in Hormone Res. 6, 111 (1951).

    Google Scholar 

  10. Bonner, J.: Synthesis of Isoprenoid Compounds in Plants. J. Chem. Educ. 26, 628 (1949).

    Article  CAS  Google Scholar 

  11. Bonner, J.: Plant Biochemistry. New York: Academic Press. 1950, p. 27.

    Google Scholar 

  12. Bonner, J. and B. Arreguin: The Biochemistry of Rubber Formation in the Guayule. I. Rubber Formation in Seedlings. Arch. Biochem. 21, 109 (1949).

    CAS  Google Scholar 

  13. Bonner, J. and A. W. Galston: The Physiology and Biochemistry of Rubber Formation in Plants. Bot. Rev. 13, 543 (1947).

    Article  CAS  Google Scholar 

  14. Chaykin, S., J. Law, A. H. Phillips, T. T. Tchen and K. Bloch: Phosphorylated Intermediates in the Synthesis of Squalene. Proc. Nat. Acad. Sci. (USA) 44, 998 (1958).

    Article  CAS  Google Scholar 

  15. Chou, T. C. and F. Lipmann: Separation of Acetyl Transfer Enzymes in Pigeon Liver Extract. J. Biol. Chem. 196, 89 (1952).

    CAS  Google Scholar 

  16. Coon, M. J., W. G. Robinson and B. K. Bachhawat: Enzymatic Studies on the Biological Degradation of the Branched Chain Amino Acids. In: Amino Acid Metabolism, p. 431. Baltimore: Johns Hopkins Press. 1955.

    Google Scholar 

  17. Cornforth, J. W. and G. Popjäk: Mechanism of Biosynthesis of Squalene from Sesquiterpenoids. Tetrahedron Letters 19, 29 (1959).

    Article  Google Scholar 

  18. Dituri, F., J. L. Rabinowitz, R. P. Hullin and S. Gurin: Precursors of Squalene and Cholesterol. J. Biol. Chem. 229, 825 (1957).

    CAS  Google Scholar 

  19. Ferguson, J. J., Jr., I. F. Durr and H. Rudney: The Biosynthesis of Mevalonic Acid. Proc. Nat. Acad. Sci. (USA) 45, 499 (1959).

    Article  CAS  Google Scholar 

  20. Hendricks, S. B., S. G. Wildman and E. J. Jones: Differentiation of Rubber and Gutta Hydrocarbons in Plant Materials. Arch. Biochem. 7, 427 (1945).

    CAS  Google Scholar 

  21. Henning, U., E. M. MÖslein> and F. Lynen: Biosynthesis of Terpenes. V. Formation of 5-Pyrophospho Mevalonic Acid by Phospho Mevalonic Kinase. Arch. Biochem. Biophys. 83, 259 (1959).

    Article  CAS  Google Scholar 

  22. Hoffman, C. H., A. F. Wagner, A. N. Wilson, E. Walton, C. H. Shunk, D. E. Wolf, F. W. Holly and K. Folkers: Synthesis of DL-3,5-Dihydroxy-3-Methylpentanoic Acid (Mevalonic Acid). J. Amer. Chem. Soc. 79, 2316 (1957).

    Article  CAS  Google Scholar 

  23. Johnston, J. A., D. W. Racusen and J. Bonner: Metabolism of Isoprenoid Precursors in a Plant System. Proc. Nat. Acad. Sci. (USA) 40, 1031 (1954).

    Article  CAS  Google Scholar 

  24. Kaplan, N. O. and F. Lipmann: The Assay and Distribution of Coenzyme A. J. Biol. Chem. 174, 37 (1948).

    CAS  Google Scholar 

  25. Kekwick, R. G. O., B. L. Archer, D. Barnard, G. M. C. Higgins, G. P. MCSweeney and C. G. Moore: Incorporation of DL-(2 C14) Mevalonic Acid Lactone into Polyisoprene. Nature 184, 268 (1959).

    Article  CAS  Google Scholar 

  26. Klosterman, H. J. and F. Smith: Isolation of β-Hydroxy-β-Methylglutaric Acid from the Seed of Flax (Linum usitatissimum). J. Amer. Chem. Soc. 76, 1229 (1954).

    Article  CAS  Google Scholar 

  27. Lipmann, F.: Acetylation of Sulfanilimide by Liver Homogenates and Extracts. J. Biol. Chem. 160, 173 (1945).

    CAS  Google Scholar 

  28. Lipmann, F., M. E. Jones, S. Black and R. M. Flynn: Enzymatic Pyrophosphory-lation of Coenzyme A by Adenosine Triphosphate. J. Amer. Chem. Soc. 74, 2384 (1952).

    Article  CAS  Google Scholar 

  29. Lynen, F., B. W. Agranoff, H. Eggerer, U. Henning und E. M. Möslein: γ,γ-Dimethyl-Allyl-Pyrophosphat und Geranyl-pyrophosphat, biologische Vorstufen des Squalens (Zur Biosynthese der Terpene, VI). Angew. Chem. 71, 657 (1959).

    Article  CAS  Google Scholar 

  30. Lynen, F., H. Eggerer, U. Henning und I. Kessel: Farnesyl-Pyrophosphat und 3-Methyl-Δ3-Butenyl-I-Pyrophosphat, die biologischen Vorstufen des Squalens (Zur Biosynthese der Terpene, III). Angew. Chem. 70, 738 (1958).

    Article  CAS  Google Scholar 

  31. Lynen, F. und U. Henning: Über den biologischen Weg zum Naturkautschuk. Angew. Chem. 72, 820 (1960).

    Article  CAS  Google Scholar 

  32. Lynen, F., E. Reichert und L. Rueff: Zum biologischen Abbau der Essigsäure VI (“Aktivierte Essigsäure”, ihre Isolierung aus Hefe und ihre chemische Natur). Liebigs Ann. Chem. 574, 1 (1951).

    Article  CAS  Google Scholar 

  33. Lynen, F., L. Wessely, O. Wieland und L. Rueff: β-Oxydation der Fettsäuren. Angew. Chem. 64, 687 (1952).

    Article  CAS  Google Scholar 

  34. Millerd, A. and J. Bonner: Acetate Activation and Acetoacetate Formation in Plant Systems. Arch. Biochem. Biophys. 49, 343 (1954).

    Article  CAS  Google Scholar 

  35. Ottke, R. C, E. L. Tatum, I. Zabin and K. Bloch: Ergosterol Synthesis in Neurospora. Federat. Proc. (Amer. Soc. exp. Biol.) 9, 212 (1950).

    Google Scholar 

  36. Park, R. B. and J. Bonner: Enzymatic Synthesis of Rubber from Mevalonic Acid. J. Biol. Chem. 233, 340 (1958).

    CAS  Google Scholar 

  37. Pollard, C, J. Bonner, A. J. Haagen-Smit and C. C. Nimmo: Transformations of Mevalonic Acid by an Enzyme System from Peas. Plant Physiol.(In press.)

    Google Scholar 

  38. Popjak, G.: Biosynthesis of Derivatives of Allylic Alcohols from 2 C14 Mevalo-nate in Liver Enzyme Preparations and Their Relation to Synthesis of Squalene. Tetrahedron Letters 19, 19 (1959).

    Article  Google Scholar 

  39. Purcell, A. E., G. A. Thompson, Jr. and J. Bonner: The Incorporation of Mevalonic Acid into Tomato Carotenoids. J. Biol. Chem. 234, 1081 (1959).

    CAS  Google Scholar 

  40. Rabinowitz, J. L. and S. Gurin: Biosynthesis of Cholesterol and β-Hydroxy-β-Methylglutaric Acid by Extracts of Liver. J. Biol. Chem. 208, 307 (1954).

    CAS  Google Scholar 

  41. Rudney, H.: The Synthesis of β-Hydroxy-β-Methylglutaric Acid in Rat Liver Homogenates. J. Amer. Chem. Soc. 76, 2595 (1954).

    Article  CAS  Google Scholar 

  42. Skeggs, H. R., L. D. Wright, E. L. Cresson, G. D. E. MacRae, C. H. Hoffman, D. E. Wolf and K. Folkers: Discovery of a New Acetate-replacing Factor. J. Bacteriol. 72, 519 (1956).

    CAS  Google Scholar 

  43. Stadtman, E. R., M. Doudoroff and F. Lipmann: The Mechanism of Acetoacetate Synthesis. J. Biol. Chem.191, 377 (1951).

    CAS  Google Scholar 

  44. Stanley, R. G.: Terpene Formation in Pine from Mevalonic Acid. Nature 182, 738 (1958).

    Article  CAS  Google Scholar 

  45. Tamura, G.: Hiochic Acid or New Growth Factor for Lactobacillus homo-hiochi and L. heterohiochi. J. Gen. Appl. Microbiol. 2, 431 (1956).

    Article  CAS  Google Scholar 

  46. Tavormina, P. A., M. H. Gibbs and J. W. Huff: The Utilization of β-Hydroxy-β-Methyl-(δ-Valerolactone in Cholesterol Biosynthesis. J. Amer. Chem. Soc.78, 4498 (1956).

    Article  CAS  Google Scholar 

  47. Tchen, T. T.: Mevalonic Kinase: Purification and Properties. J. Biol. Chem.233, 1100 (1958).

    CAS  Google Scholar 

  48. Teas, H. J. and J. Bonner: Rubber Biosynthesis. Revue Generale du Caoutchouc 37, 1143 (1960).

    CAS  Google Scholar 

  49. Teas, H. J., L. Polhemus and J. C. Montermoso: Abstr., Conference on Radioactive Isotopes in Agriculture, (U. S. Dept. of Agric), January, 1956.

    Google Scholar 

  50. Thompson, G. A., Jr., A. E. Purcell and J. Bonner: A Carotene Precursor; its Proposed Structure and Place in Biosynthetic Sequence. Plant Physiol. 35, 678 (1960).

    Article  CAS  Google Scholar 

  51. Witting, L. A. and J. W. Porter: A Geraniol Derivative—An Intermediate in the Biosynthesis of Squalene by a Rat Liver Enzyme System. Biochem. Biophys. Res. Comm.1, 341 (1959).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1963 Springer-Verlag/Wien

About this chapter

Cite this chapter

Bonner, J. (1963). The Biosynthesis of Rubber. In: Zechmeister, L. (eds) Progress in the Chemistry of Organic Natural Products/Progrès Dans La Chimie Des Substances Organiques Naturelles. Fortschritte Der Chemie Organischer Naturstoffe, vol 21. Springer, Vienna. https://doi.org/10.1007/978-3-7091-7149-3_1

Download citation

  • DOI: https://doi.org/10.1007/978-3-7091-7149-3_1

  • Publisher Name: Springer, Vienna

  • Print ISBN: 978-3-7091-7150-9

  • Online ISBN: 978-3-7091-7149-3

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics