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Transformation of Prostaglandin D 2 to 11‐Dehydro Thromboxane B 2 by Baeyer‐Villiger Oxidation
Author(s) -
Nakashima Fumie,
Schneider Claus
Publication year - 2020
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1002/lipd.12206
Subject(s) - chemistry , thromboxane , metabolite , cyclopentanone , prostaglandin , prostaglandin h2 , arachidonic acid , thromboxane a2 , stereochemistry , thromboxane a synthase , medicinal chemistry , biochemistry , platelet , enzyme , medicine , receptor , catalysis
Prostaglandin D 2 is one of five chief prostanoids formed in the cyclooxygenase pathway of arachidonic acid oxidation. Except for a single oxygen atom, PGD 2 is structurally identical to 11‐dehydro thromboxane B 2 (11d‐TxB 2 ), a urinary metabolite of the pro‐aggregatory platelet activator, thromboxane A 2 . The close structural relationship suggested that one might be transformed to the other. Accordingly, we tested whether the cyclopentanone of PGD 2 can be expanded to the δ‐lactone of 11d‐TxB 2 in a Baeyer‐Villiger oxidation. Oxidation of PGD 2 with two standard oxidants showed that 11d‐TxB 2 was formed only with H 2 O 2 but not with peracetic acid. Byproducts of the H 2 O 2 ‐mediated oxidation were hydroperoxide derivatives and isomers of PGD 2 . Chemical oxidation of PGD 2 to 11d‐TxB 2 may be a model for an equivalent enzymatic transformation, suggesting a possible link in the metabolism of PGD 2 and thromboxane A 2 .