High-field 1H NMR studies of prostaglandin H2 and its decomposition pathways.
Prostaglandin H2 displays at 500 MHz a detailed 1H-NMR in which all methylene groups are non-equivalent in C6D6 solution. The spectrum was assigned by analogy to isosteric structures. The dissymmetric perturbation and steric hindrance of the bicyclo [2.2.1] core caused by the side-chains provides a rationale for the selective fragmentations which PGH2 undergoes. Purified PGH2 is considerably more robust than previous literature accounts suggest. The following transformations were monitored by 1H-NMR: 1) O-O bond cleavage by Ph3P , 2) aqueous media fragmentation to PGE2 and PGD2, 3) base catalyzed fragmentation to ketoaldehydes , and 4) thermolysis attempts.
D055598:Chemical Phenomena; D002621:Chemistry; D015237:Dinoprost; D015232:Dinoprostone; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015230:Prostaglandin D2; D011449:Prostaglandin Endoperoxides; D011450:Prostaglandin Endoperoxides, Synthetic; D044262:Prostaglandin H2; D011457:Prostaglandins D; D011458:Prostaglandins E; D011460:Prostaglandins F; D011463:Prostaglandins H
D011449:Prostaglandin Endoperoxides; D011450:Prostaglandin Endoperoxides, Synthetic; D011457:Prostaglandins D; D011458:Prostaglandins E; D011460:Prostaglandins F; D011463:Prostaglandins H; D044262:Prostaglandin H2; C041344:prostaglandin H2 methyl ester; D015237:Dinoprost; D015232:Dinoprostone; D015230:Prostaglandin D2