Abstract
The conformations of prostacyclin, PGI2, and three of its analogues, 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, [Formula: see text] for 6R-PGI1, and 6E/11E for 6S-PGI1, and carbacyclin. The data indicate that each molecule adopts a narrow pseudolibrational range, if not a single conformation. The α- and ω-side chain conformations were characterized, but not unambiguously. Vicinal coupling constants and nuclear Overhauser enhancements proved to be the most useful spectroscopic parameters in this study.
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