Controlled Tetradeuteration of Straight‐Chain Fatty Acids: Synthesis, Application, and Insight into the Metabolism of Oxidized Linoleic Acid

We describe a concise and reliable protocol for the precisely controlled tetradeuteration of straight-chain fatty acids (FAs) at α- β-positions that is generally applicable to variety FAs, including trans-FAs, polyunsaturated FAs (PUFAs), their oxidized derivatives. The introduction four deuterium atoms into enables persistent quantitative tracking by LC-MS/MS analysis based on molecular structures. In addition, phosphatidylcholine (PC) species prepared from tetradeuterated thus obtained give diagnostic peak, namely, phosphocholine fragment contains deuterium, in analysis. With these features, metabolism representative linoleic acid, is, hydroxyoctadecadienoic acid (HODE), was investigated, leading identification acyltransferases transfer acyl moiety derived HODE lysophosphatidylcholine.