Transformation of Prostaglandin D₂ to 11-Dehydro Thromboxane B₂ by Baeyer-Villiger Oxidation.

ABSTRACT: 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 H₂ O₂ but not with peracetic acid. Byproducts of the H₂

SUBMITTER: Nakashima F 

PROVIDER: S-EPMC7153723 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature