ing 13(S)-HPODE. 1-stearoyl-sn-glycero-3 phosphocholine was first generated by a
chemo-enzymatic approach involving lipases. The protected HPOD was then ligated
through DCC-DMAP methodology which, after deprotection, afforded the target
compound 12 : 1 stearoyl-2-[13’(S)-hydroperoxy-(9’Z,11’E)-octadecadienoyl]-sn-
glycero-3-phosphocholine (Figure 18).
16.4.4 Exploiting the double dioxygenation of arachidonic acid
In 1989, Corey and co-workers (Corey et al., 1989) exploited the SBLOX-1 double
dioxygenation of AA to realize a simple synthesis of lipoxin A 4 , an important phy-
siologically active eicosanoid of the AA cascade. As seen previously (Section
16.3.1), the double dioxygenation affords after chemical reduction, two dihydroxy
354 16 Properties and Applications of Lipoxygenases
Figure 18. Last steps synthesis of the HPOD phospholipid 12 (Baba et al., 1990).
Figure 19. Chemoenzymatic synthesis of lipoxin A 4 (Corey et al., 1989).