M. Hamberg, B. Samuelsson
Nov 25, 1967
Citations
1
Influential Citations
342
Citations
Quality indicators
Journal
The Journal of biological chemistry
Abstract
Abstract The mechanism of the conversion of 8,11,14-eicosatrienoic acid into prostaglandin E1 (PGE1) and prostaglandin F1α (PGF1α) has been studied. Incubation of [13d-3H,3-14C]- and [13l-3H,3-14C]8,11,14-eicosatrienoic acids showed that the hydrogen removed from C-13 during the conversion into PGE1 and PGF1α has the l configuration. The conversion of [13l-3H,3-14C]8,11,14-eicosatrienoic acid into PGE1 is accompanied by a hydrogen isotope effect. No conversion of [2-14C]15l-hydroperoxy-8(cis),11(cis),13(trans)-eicosatrienoic acid or [2-14C]15l-hydroxy-8(cis), 11(cis),13(trans)-eicosatrienoic acid into PGE1 or PGF1α could be detected. Incubations of [9-3H,3-14C]8,11,14-eicosatrienoic acid revealed that PGF1α is not formed via PGE1 in the system used. The mechanistic implications of the results obtained are discussed. It is suggested that 11-peroxy-8,12,14-eicosatrienoic acid is the first intermediate in the conversion. The peroxy acid is cyclized into an endoperoxide, which is eventually transformed into PGE1 or PGF1α by independent reactions.