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Transformation of Prostaglandin D 2 to 11-Dehydro Thromboxane B 2 by Baeyer-Villiger Oxidation
Ist Teil von
Lipids, 2020-01, Vol.55 (1), p.73-78
Ort / Verlag
United States
Erscheinungsjahr
2020
Quelle
MEDLINE
Beschreibungen/Notizen
Prostaglandin D
is one of five chief prostanoids formed in the cyclooxygenase pathway of arachidonic acid oxidation. Except for a single oxygen atom, PGD
is structurally identical to 11-dehydro thromboxane B
(11d-TxB
), a urinary metabolite of the pro-aggregatory platelet activator, thromboxane A
. The close structural relationship suggested that one might be transformed to the other. Accordingly, we tested whether the cyclopentanone of PGD
can be expanded to the δ-lactone of 11d-TxB
in a Baeyer-Villiger oxidation. Oxidation of PGD
with two standard oxidants showed that 11d-TxB
was formed only with H
O
but not with peracetic acid. Byproducts of the H
O
-mediated oxidation were hydroperoxide derivatives and isomers of PGD
. Chemical oxidation of PGD
to 11d-TxB
may be a model for an equivalent enzymatic transformation, suggesting a possible link in the metabolism of PGD
and thromboxane A
.