On the Absolute Configuration of 19‐Hydroxy‐Prostaglandin B1
Open Access
- 1 October 1968
- journal article
- Published by Wiley in European Journal of Biochemistry
- Vol. 6 (1) , 147-150
- https://doi.org/10.1111/j.1432-1033.1968.tb00431.x
Abstract
19‐Hydroxy‐prostaglandin B1, isolated from human seminal plasma, was treated with tritiumlabeled acetic anhydride and degraded by oxidation with permanganate in acetone. Tritiumlabeled 3‐acetoxybutanoic acid was isolated from the oxidation product and diluted with unlabeled dl‐3‐acetoxybutanoic acid. The morphine salt of the acid was resolved. These experiments showed that the tritium‐labeled 3‐acetoxybutanoic acid had the d‐configuration and consequently the parent 19‐hydroxy‐prostaglandin B1 has the d‐configuration at C‐19. The configuration at C‐15 is discussed.Keywords
This publication has 8 references indexed in Scilit:
- The identification of prostaglandins E2, F2α and A2 from rabbit kidney medullaBiochemical Journal, 1967
- The Effect of Eight New Prostaglandins on Human MyometriumActa Physiologica Scandinavica, 1967
- Absolute Configuration of the ProstaglandinsNature, 1966
- Prostaglandins in Human Seminal PlasmaPublished by Elsevier ,1966
- Isolation and structure of a new prostaglandin from human seminal plasma. Prostaglandins and related factors 43Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism, 1965
- Prostaglandins and Related FactorsJournal of Biological Chemistry, 1963
- A Method for the Determination of the Structure of Saturated Branched-Chain Fatty AcidsAustralian Journal of Chemistry, 1959
- The specification of asymmetric configuration in organic chemistryCellular and Molecular Life Sciences, 1956