67910-12-7Relevant academic research and scientific papers
Transformation of Prostaglandin D2 to 11-Dehydro Thromboxane B2 by Baeyer-Villiger Oxidation
Nakashima, Fumie,Schneider, Claus
, p. 73 - 78 (2020)
Prostaglandin D2 is one of five chief prostanoids formed in the cyclooxygenase pathway of arachidonic acid oxidation. Except for a single oxygen atom, PGD2 is structurally identical to 11-dehydro thromboxane B2 (11d-TxB2), a urinary metabolite of the pro-aggregatory platelet activator, thromboxane A2. The close structural relationship suggested that one might be transformed to the other. Accordingly, we tested whether the cyclopentanone of PGD2 can be expanded to the δ-lactone of 11d-TxB2 in a Baeyer-Villiger oxidation. Oxidation of PGD2 with two standard oxidants showed that 11d-TxB2 was formed only with H2O2 but not with peracetic acid. Byproducts of the H2O2-mediated oxidation were hydroperoxide derivatives and isomers of PGD2. Chemical oxidation of PGD2 to 11d-TxB2 may be a model for an equivalent enzymatic transformation, suggesting a possible link in the metabolism of PGD2 and thromboxane A2.
