Abstract
The distribution of isotopic labels inn-heptadecane enriched from [1,2-13C] and [2-13C, 2-2H3) acetates byAnacystis nidulans has been determined by13C nuclear magnetic resonance (13C NMR). Labeling with [1,2-13C] acetate is consistent with assembly from13C−13C units derived from an acetate “starter” group and 8 malonate units, as in fatty acid biosynthesis, followed by production of a methyl group through bond cleavage of the terminal13C−13C unit. A comparison of the hydrocarbon with palmitic acid (the only fatty acid produced in sufficient amount for NMR analysis) enriched from [2-13C,2-2H3]acetate by the same culture shows that they have retained the same fraction of2H at corresponding sites, and have therefore undergone identical biosynthetic and hydrogen-deuterium exchange processes, as would be expected ifn-heptadecane originates from de novo-synthesized stearic acid.
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References
“Chemistry and Biochemistry of Natural Waxes”, edited by P.E. Kolattukudy, Elsevier North Holland, Amsterdam, 1976.
Kolattukudy, P.E., “Proc. Symp. on Sources, Effects and Sinks of Hydrocarbons in the Aquatic Environment”, The American Institute of Biological Sciences, 1976, p. 120.
Bird, C.W., and J.M. Lynch, Chem. Soc. Rev. 3:309 (1974).
Han, J., H.W.S. Chan and M. Calvin, J. Am. Chem. Soc. 91:5156 (1969).
Kolattukudy, P.E., J.S. Buckner and L. Brown, Biochem. Biophys. Res. Commun. 47:1306 (1972).
McInnes, A.G., J.A. Walter and J.L.C. Wright, Tetrahedron Lett. 35:3245 (1979).
Nomenclature of Organic Chemistry, Section H, International Union of Pure and Applied Chemistry, Organic Chemistry Division, Prepared for Publication by J. Rigaudy and S.P. Klesney, Pergamon, New York, 1979.
Allen, M.M., J. Phycol. 4:1 (1968).
Kratz, W.A., and J. Myers, Am. J. Bot. 42:282 (1955).
Laycock, M.V., and J.L.C. Wright, in preparation.
Paul, E.G., and D.M. Grant, J. Am. Chem. Soc. 85:1701 (1963).
Grant, D.M., and E.G. Paul, J. Am. Chem. Soc. 86:2984 (1964).
Tulloch, A.P., Can. J. Chem. 55:1135 (1977).
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NRCC No. 18251.
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McInnes, A.G., Walter, J.A. & Wright, J.L.C. Biosynthesis of hydrocarbons by algae: Decarboxylation of stearic acid to N-heptadecane inAnacystis nidulans determined by13C- and2H-labeling and13C nuclear magnetic resonance. Lipids 15, 609–615 (1980). https://doi.org/10.1007/BF02534009
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DOI: https://doi.org/10.1007/BF02534009