Biosynthesis of hydrocarbons by algae: Decarboxylation of stearic acid to N‐heptadecane inAnacystis nidulans determined by13C‐ and2H‐labeling and13C nuclear magnetic resonance

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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.