Abstract
Racemic 11-hydroxylauric acid was obtained in a two-step synthesis and derivatized to diastereoisomeric ( S)-α-methoxy-α-trifluoromethylphenylacetate esters of methyl 11-hydroxylaurate, which were readily resolved by isocratic normal-phase high-performance liquid chromatography (HPLC). The assignment of absolute configuration of each diastereoisomer was carried out using proton NMR spectroscopy and a lanthanide shift reagent. From this result, an analytical method was designed for the determination of the stereochemical outcome of (ω — 1) lauric acid hydroxylation mediated by rat liver microsomes. 14C-labelled ω- and (ω — 1)-hydroxylated lauric acids were separated by reversed-phase HPLC and quantified by liquid scintillation counting. Enantiomeric (ω — 1)-methyl laurates were derivatized into their diastereoisomeric ( S)-MTPA esters, resolved and quantified by HPLC. Some typical inducers of cytochrome P-450 were used and their effects on lauric acid hydroxylase activity, regioselectivity and stereoselectivity were shown.
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