Front Matter

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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).

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