Journal of Lipid Research, Vol 24, 938-941, Copyright © 1983 by Lipid Research, Inc.
Synthesis of carbon-13-labeled tetradecanoic acids
JT Sparrow, KM Patel and JD Morrisett
The synthesis of tetradecanoic acid enriched with 13C at carbons 1, 3, or 6
is described. The label at the carbonyl carbon was introduced by treating
1-bromotridecane with K13CN (90% enriched) to form the 13C- labeled
nitrile, which upon hydrolysis yielded the desired acid. The [3-
13C]tetradecanoic acid was synthesized by alkylation of diethyl sodio-
malonate with [1-13C]1-bromododecane; the acid was obtained upon
saponification and decarboxylation. The label at the 6 position was
introduced by coupling the appropriately labeled alkylcadmium chloride with
the half acid chloride methyl ester of the appropriate dioic acid, giving
the corresponding oxo fatty acid ester. Formation of the tosylhydrazone of
the oxo-ester followed by reduction with sodium cyanoborohydride gave the
labeled methyl tetradecanoate which, upon hydrolysis, yielded the desired
tetradecanoic acid. All tetradecanoic acids were identical to unlabeled
analogs as evaluated by gas-liquid chromatography and infrared or NMR
spectroscopy. These labeled fatty acids were used subsequently to prepare
the correspondingly labeled diacyl phosphatidylcholines.
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