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

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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.

References (17)

  • D.H. Nugteren et al.

    Biochem. Biophys. Acta

    (1973)
  • D.A. van Dorp
  • N.H. Andersen et al.

    Prostaglandins

    (1977)
  • M. Hamberg et al.
  • M. Hamberg et al.
  • R.A. Johnson et al.

    J. Am. Chem. Soc

    (1977)
  • N.A. Porter et al.

    J. Am. Chem. Soc

    (1979)
  • D.J. Coughlin et al.

    J. Am. Chem. Soc

    (1977)
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