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

Niels H. Andersen; Cynthia J. Hartzell

doi:10.1016/0006-291X(84)91284-1

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

Niels H. Andersen, Cynthia J. Hartzell

Research output: Contribution to journal › Article › peer-review

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 language	English (US)
Pages (from-to)	512-519
Number of pages	8
Journal	Biochemical and Biophysical Research Communications
Volume	120
Issue number	2
DOIs	https://doi.org/10.1016/0006-291X(84)91284-1
State	Published - Apr 30 1984
Externally published	Yes

ASJC Scopus subject areas

Biophysics
Biochemistry
Molecular Biology
Cell Biology

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title = "High-field 1H NMR studies of prostaglandin H2 and its decomposition pathways",

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.",

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AB - 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.

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