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The Metabolism, Structure, and Function of Plant Lipids pp 553–555Cite as

Mechanism of Biosynthesis of ß-Diketones and Alkan-2-OL Esters from Epicuticular Waxes

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Abstract

Long chain aliphatic ß-diketones and alkan-2-ol esters are common constituents of plant surface lipids1. The ß-dicarbonyl pattern, two carbonyl groups 1, 3 one another, has suggested that the biosynthesis of ß-diketones involves condensation of appropriate ß-ketoesters and esters, via a ‘biological Claisen reaction’2. An alternative route has been advanced according to which ß-diketones are generated by an elongation-decarboxylation reaction on a protected ß-keto acid precursor3.

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References

  1. G. Bianchi and M.L. Figini, J. Agric.Food Chemistry 34: 429 (1986).

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  2. G. Bianchi and M. Corbellini, Phytochemistry 16: 943 (1977).

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  3. P. von Wettstein-Knowles in “Biochemistry and Metabolism of Plant Lipids”. J.F.G.M. Wintermans and P.J.C. Kuiper, eds. Elsevier Biomedical Press B.V. and references therein cited, 69 (1982).

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  4. J. March, in “Advanced Organic Chemistry” (Mc Graw-Hill Kogakusha) (a) pp. 1037-1044; (b) p. 506 (1977).

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  5. G. Bianchi, unpublished results.

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  6. P. Dennif and D.A. Whiting, J.C.S. Chem.Comm. 711 (1976).

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  7. G. Bianchi and M. Grugni, Gazz. Chim. Ital. 115: 633 (1985).

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  8. G. Bianchi, Genet. Agr. 39: 471 (1985).

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Author information

Authors and Affiliations

  1. Dipartimento di Chimica Organica, Università, I-27100, Pavia, Italy

    Giorgio Bianchi

Authors
  1. Giorgio Bianchi
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Editors and Affiliations

  1. University of California, Davis, Davis, California, USA

    Paul K. Stumpf

  2. ARCO Plant Cell Research Institute, Dublin, California, USA

    J. Brian Mudd

  3. U.S. Department of Agriculture, Albany, California, USA

    W. David Nes

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© 1987 Plenum Press, New York

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Bianchi, G. (1987). Mechanism of Biosynthesis of ß-Diketones and Alkan-2-OL Esters from Epicuticular Waxes. In: Stumpf, P.K., Mudd, J.B., Nes, W.D. (eds) The Metabolism, Structure, and Function of Plant Lipids. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-5263-1_102

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  • DOI: https://doi.org/10.1007/978-1-4684-5263-1_102

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4684-5265-5

  • Online ISBN: 978-1-4684-5263-1

  • eBook Packages: Springer Book Archive

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