CHEMOENZYMATIC PRODUCTION OF (-CORIOLIC ACID FROM TRILINOLEIN - COUPLED SYNTHESIS AND EXTRACTION())

Chemoenzymatic conversion of trilinolein to (+)-coriolic acid was inve stigated in this work. Lipase-catalyzed hydrolysis of trilinolein and lipoxygenation of liberated linoleic acid were coupled in a two-phase medium that consisted of a pH 9 berate buffer and a water-immiscible o rganic solvent (octane). High concentrations of trilinolein could be d issolved in the organic phase (up to 340 mM). Linoleic acid, liberated after hydrolysis, transferred to the aqueous phase and was enzymatica lly converted to the preferred 13(S)-hydroperoxy-9Z,11E-octadecadienoi c acid with soybean lipoxygenase-l. This product, which remained in th e aqueous phase, could be recovered by centrifugation and then chemica lly reduced to (+)-coriolic acid (purity >95%). Recovery of this compo und by liquid-liquid extraction was easy. The structure of (+)-corioli c acid has been confirmed by H-1 nuclear magnetic resonance spectrosco py, mass spectrometry, and infrared spectroscopy. High yields were obt ained with pure trilinolein or sunflower oil as initial substrates.