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On the Mechanism of the Biosynthesis of Prostaglandins E1 and F1α
Open accessAbstract
The mechanism of the conversion of 8,11,14-eicosatrienoic acid into prostaglandin E1 (PGEl) and prostaglandin F1, (PGFI,) has been studied.Incubation of [13~-~H,3-"C]and [13~-3H ,3J*C]8,11,14-eicosatrienoic acids showed that the hydrogen removed from C-13 during the conversion into PGEl and PGFI, has the L configuration.The conversion of [13~-3H ,3J4C]8, 11,14-eicosatrienoic acid into PGEl is accompanied by a hydrogen isotope effect.No conversion of [ 2 J*C]lSL-hydroperoxy -8(cis), ll(cis) ,13(trans) -eicosatrienoic acid or [2-'*C]lSL-hydroxy-8(cis), ll(cis) , lJ(frans)eicosatrienoic acid into PGEl or PGFI, could be detected.Incubations of [9-3H ,3J4C]8,11 ,14-eicosatrienoic acid revealed that PGF1, is not formed via PGEl 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 PGEl or PGF,, by independent reactions.
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Cited by
Assay for lipid peroxides in animal tissues by thiobarbituric acid reaction
Ohkawa, H., Ohishi, N., & Yagi, K. (1979) · Analytical Biochemistry · doi:10.1016/0003-2697(79)90738-3 · Cited by 29,297
Cyclooxygenases: Structural, cellular, and molecular biology
Smith, W. L., DeWitt, D. L., & Garavito, R. M. (2000) · Annual Review of Biochemistry · doi:10.1146/annurev.biochem.69.1.145 · Cited by 2,925
Mechanism for irreversible self-deactivation of prostaglandin synthetase.
Egan, R. W., Paxton, J., & Kuehl, F. A. (1976) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(17)32853-3 · Cited by 586
Marnett, L. J. (2000) · Current Opinion in Chemical Biology · doi:10.1016/s1367-5931(00)00130-7 · Cited by 151
CADENAS, E., SIES, H., NASTAINCZYK, W., & ULLRICH, V. (1983) · Hoppe-Seyler´s Zeitschrift für physiologische Chemie · doi:10.1515/bchm2.1983.364.1.519 · Cited by 108
Metadata
- Authors
- Hamberg, M., & Samuelsson, B.
- Venue
- Journal of Biological Chemistry
- Publisher
- Elsevier BV
- Published
- 1967-11
- Volume
- 242
- Issue
- 22
- Pages
- 5336-5343
- ISSN
- 0021-9258 (ISSN-L)
- OpenAlex
- W1531513729
- Cited by
- 402
- References
- 0
- FWCI
- 2.60
- Type
- journal article
- Language
- en
- Open access
- hybrid
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- Hamberg, M., & Samuelsson, B. (1967). On the Mechanism of the Biosynthesis of Prostaglandins E1 and F1α. Journal of Biological Chemistry. https://doi.org/10.1016/s0021-9258(18)99433-0
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