On the mechanism of biosynthesis of leukotrienes and related compounds

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Abstract
[10D‐3H; 3‐14C]‐ and [10L‐3H; 3‐14C]arachidonic acids were incubated with human polymorphonuclear leukocytes and with human platelets. Leukotriene B4 and 5(S),12(S)‐dihydroxy‐6trans,8cis,10trans,14‐cis‐eicosatetraenoic acid (5,12‐DHETE) were isolated and the 3H/14C ratios determined. It could be concluded that the 10D (pro‐R)‐hydrogen is eliminated in the conversion of 5(S)‐hydroperoxy‐6trans,8cis,11cis,14cis‐eicosatetraenoic acid into leukotriene A4 whereas in the conversion of arachidonic acid into 5,12‐DHETE the 10L (pro‐S)‐hydrogen is lost. Incubation of the doubly labeled arachidonic acids with human platelets confirmed and extended previous data on the stereochemistry of the hydrogen removal from C‐10 during the conversion into 12(S)‐hydroperoxy‐5cis,8cis,10trans,14cis‐eicosatetraenoic acid, i.e., the 10L (pro‐S)‐hydrogen is eliminated and the 10D (pro‐R)‐hydrogen retained.