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On the mechanism of biosynthesis of leukotrienes and related compounds
Author(s) -
Panossian Alexander,
Hamberg Mats,
Samuelsson Bengt
Publication year - 1982
Publication title -
febs letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.593
H-Index - 257
eISSN - 1873-3468
pISSN - 0014-5793
DOI - 10.1016/0014-5793(82)80801-6
Subject(s) - arachidonic acid , incubation , biosynthesis , chemistry , platelet , hydrogen , leukotriene , biochemistry , stereochemistry , biology , organic chemistry , enzyme , immunology , asthma
[10D‐ 3 H; 3‐ 14 C]‐ and [10L‐ 3 H; 3‐ 14 C]arachidonic acids were incubated with human polymorphonuclear leukocytes and with human platelets. Leukotriene B 4 and 5( S ),12( S )‐dihydroxy‐6 trans ,8 cis ,10 trans ,14‐ cis ‐eicosatetraenoic acid (5,12‐DHETE) were isolated and the 3 H/ 14 C ratios determined. It could be concluded that the 10D ( pro‐R )‐hydrogen is eliminated in the conversion of 5( S )‐hydroperoxy‐6 trans ,8 cis ,11 cis ,14 cis ‐eicosatetraenoic acid into leukotriene A 4 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‐5 cis ,8 cis ,10 trans ,14 cis ‐eicosatetraenoic acid, i.e., the 10L ( pro‐S )‐hydrogen is eliminated and the 10D ( pro‐R )‐hydrogen retained.