High-field 1H NMR studies of prostaglandin H2 and its decomposition pathways |
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Authors: | N H Andersen C J Hartzell |
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Affiliation: | Department of Chemistry, University of Washington Seattle, Washington 98195 USA |
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Abstract: | 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. |
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