OPTIMIZATION OF LARGE-SCALE PREPARATION OF 13-(S)-HYDROPEROXY-9Z,11E-OCTADECADIENOIC ACID USING SOYBEAN LIPOXYGENASE - APPLICATION TO THE CHEMOENZYMATIC SYNTHESIS OF (+)-CORIOLIC ACID

The optimization of 13-S-hydroperoxy-9Z,11E-octadecadienoic acid synthesis is described using lipoxygenase-1 from soybeans at high substrate concentration. The optimal values of the tested parameters are as follows: oxygen pressure 2.5 bar, temperature 5 degrees C, pH 11, enzyme concentration 4 mg/ml and substrate concentration 0.1 M. All these values were used in a single reaction, allowing chemoenzymatic synthesis of gram amounts of(+)-coriolic acid (99%, e.e. 97%) with a 54% yield starting from linoleic acid.