E. Granström, W. Lands, B. Samuelsson
Aug 10, 1968
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Influential Citations
64
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Journal
Journal of Biological Chemistry
Abstract
Abstract Incubation of 8,11,14-eicosatrienoic acid with homogenates of sheep vesicular gland yielded a new product, which has been identified as 9α, 15-dihydroxy-11-ketoprost-13-enoic acid. The identification was based on mass spectrometry of the methyl ester and the methoxime derivative, and on infrared spectroscopy and ultraviolet spectroscopy, before and after treatment with alkali. Reduction of the isolated compound with borodeuteride yielded prostaglandin F1α containing deuterium in the ring, as established by mass spectrometry of a derivative. Further proof for the location of the keto group in the isomer was obtained through biosynthesis from [9-3H,3-14C]- and [11-3H,2-14C]8,11,14-eicosatrienoic acids. Incubation with [13D-3H,3-14C]8,11, 14-eicosatrienoic acid revealed that the 13d-hydrogen atom is retained during the formation of the isomer, which is also the case with prostaglandin E1. The mechanism of the conversion of 8,11,14-eicosatrienoic acid into prostaglandins is discussed. The identification of 9α,15-dihydroxy-11-ketoprost-13-enoic acid and the finding that 3H at C-9 is retained during its formation further support the involvement of an endoperoxide in the biosynthesis of prostaglandins.