High-field 1H NMR studies of prostaglandin H2 and its decomposition pathways

Niels H. Andersen, Cynthia J. Hartzell

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12 Scopus citations

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) OO bond cleavage by Ph3P, 2) aqueous media fragmentation to PGE2 and PGD2, 3) base catalyzed fragmentation to ketoaldehydes, and 4) thermolysis attempts.

Original languageEnglish (US)
Pages (from-to)512-519
Number of pages8
JournalBiochemical and Biophysical Research Communications
Volume120
Issue number2
DOIs
StatePublished - Apr 30 1984
Externally publishedYes

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ASJC Scopus subject areas

  • Biophysics
  • Biochemistry
  • Molecular Biology
  • Cell Biology

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