Abstract
The β-oxidation of an unsaturated fatty acid containing conjugated double bonds at odd-numbered carbon atoms has not previously been studied. It is, therefore, not clear whether, during the β-oxidation of such an acid, the double bonds will be isomerized by enoyl-CoA isomerase (Δ3-Δ2-enoyl-CoA isomerase) with the loss or retention of its conjugated nature. To investigate the problem, (E,E)-3,5-octadienoyl-CoA was synthesized for use as a model substrate, and enoyl-CoA isomerase was partially purified from bovine liver. The isomerization was followed by spectrophotometric and gas liquid chromatographic methods, and the results suggested that the isomerization of the model substrate proceeded with retention of a conjugated double bond system. It is, therefore, proposed that the β-oxidation intermediate of α-eleostearic acid (Δ9,11,13 fatty acid) will also isomerize with retention of the conjugated double bond system.
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References
Green, D.E., and D.W. Allmann, in “Metabolic Pathways,” Vol. 2, Edited by D.M. Greenberg, Academic Press, New York, 1968, p. 11.
Bishop, D.G., and P.K. Stumpf, Biochem. Methodol. Lipids, 361–390 (1971).
Hitchcock, C., and B.W. Nichols, in “Plant Lipid Biochemistry,” Academic Press, New York, 1971, p. 201.
Galliard, T., and E.I. Mercer, in “Recent Advances in the Chemistry and Biochemistry of Plant Lipids”, Academic Press, London, 1975, p. 332.
Stoffel, W., R. Ditzer, and H. Caesar, Hoppe-Seyler's Z. Physiol. Chem. 339:167 (1964).
Kunau, W.H., Angew. Chem. Intl. Ed. Engl. 15:61 (1976).
Du Plessis, L.M., and S. Vladár, S. Afr. J. Sci. 70:183 (1974).
Wehmeyer, A.S., South African Plants No. 4463,000-0010. Addendum 1, Pretoria: Division of Agricultural Information (1976).
Struijk, C.B., and R.K. Beerthuis, Biochim. Biophys. Acta 116:12 (1966).
Stoffel, W., and W. Ecker, in “Methods in Enzymology”, Vol. 14, Edited by J.M. Lowenstein, Academic Press, New York, 1969, p. 99.
Kuhn, R., and M. Hoffer, Ber. 65:170 (1932).
Du Plessis, L. M., and J.A.D. Erasmus, S. Afr. J. Chem. 31:75 (1978).
Goldman, P., and P.R. Vagelos, J. Biol. Chem. 236:2620 (1961).
Stahl, E., in “Thin layer chromatography”, 2nd ed., Springer Verlag, Berlin, 1969, p. 890.
Stadtman, E.R., in “Methods in Enzymology,” Vol. 3, Edited by S.P. Colowick and N.O. Kaplan, Academic Press, New York, 1957, p. 931.
Pullman, M.E., Anal. Biochem. 54:188 (1973).
Lipmann, F., and L.C. Tuttle, J. Biol. Chem. 159:21 (1945).
Rilling, H.C., and M.J. Coon, J. Biol. Chem. 235:3087 (1960).
McGrath, R.M., Anal. Biochem. 49:95 (1972).
Du Plessis, L.M., and P.J. van Wyk, S. Afr. J. Sci. To be published.
Zeman, A., and H. Scharmann, Fette, Seifen, Anstrichm. 74:509 (1972).
Crombie, L., J. Chem. Soc. 1:1007 (1955).
Lynen, F., Fed. Proc. 12:683 (1953).
Wakil, S.J., and G. Hübscher, J. Biol. Chem. 235:1554 (1960).
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Part of doctoral thesis submitted to University of Pretoria, Pretoria, 0001, Republic of South Africa.
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Du Plessis, L.M., Grobbelaar, N. Isomerization of the double bonds of a conjugated fatty acid during β-oxidation. Lipids 14, 943–948 (1979). https://doi.org/10.1007/BF02533510
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DOI: https://doi.org/10.1007/BF02533510