Chemistry of Prostaglandins and Thromboxanes

Abstract

The structures of several prostaglandins were determined during the early 1960’s. First, two biologically active compounds were isolated from sheep vesicular glands; these compounds were called PGE₁ and PGF_1α (for a review, see Ref. 1). Reduction of PGE₁ with sodium borohydride gave a mixture of two epimeric compounds, PGF_1α and PGF_1β. Further studies on the structures of these compounds revealed that they were derivatives of a C₂₀ carboxylic acid, later named prostatic acid, which contained a five-membered ring (C-8 to C-12) with two side chanis. Prostaglandins of the E type were shown to have a keto group at C-9, whereas a hydroxyl group was found in this position in the F prostaglandins. The index α or β indicates the stereochemical position of this hydroxyl group. Common to all these prostaglandins and most others is the presence of an L-hydroxyl group at C-15 and a Δ¹³-trans double bond.