The conformations of prostacyclin and related prostaglandins
- 1 May 1985
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 63 (5) , 1143-1149
- https://doi.org/10.1139/v85-194
Abstract
The conformations of prostacyclin, PGI2, and 3 of its analogs 6R- and 6S-PGI1 and carbacyclin, were studied by high field 1H NMR spectroscopy. The cis-bicyclo- and cis-oxabicyclo[3,3,0]octane ring conformations were completely assigned. The minima for the pseudorotational conformations are observed at 7E/12E for PGI2, .**GRAPHIC**. for 6R-PGI1 and 6E/11E for 6S-PGI1 and carbacyclin. Each molecule adopts a narrow pseudolibrational range, if not a single conformation. The .alpha.- and .omega.-side chain conformations were characterized, but not unambiguously. Vicinal coupling constants and nuclear Overhauser enhancements proved to be the most useful spectroscopic parameters.This publication has 1 reference indexed in Scilit:
- Synthesis and characterization of prostacyclin, 6-ketoprostaglandin F1.alpha., prostaglandin I1, and prostaglandin I3Journal of the American Chemical Society, 1978