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 | |
| State | Published - Apr 30 1984 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Biochemistry
- Biophysics
- Molecular Biology
Cite this
High-field 1H NMR studies of prostaglandin H2 and its decomposition pathways. / Andersen, Niels H.; Hartzell, Cynthia J.
In: Biochemical and Biophysical Research Communications, Vol. 120, No. 2, 30.04.1984, p. 512-519.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - High-field 1H NMR studies of prostaglandin H2 and its decomposition pathways
AU - Andersen, Niels H.
AU - Hartzell, Cynthia J
PY - 1984/4/30
Y1 - 1984/4/30
N2 - 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.
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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U2 - 10.1016/0006-291X(84)91284-1
DO - 10.1016/0006-291X(84)91284-1
M3 - Article
C2 - 6587849
AN - SCOPUS:0021289055
VL - 120
SP - 512
EP - 519
JO - Biochemical and Biophysical Research Communications
JF - Biochemical and Biophysical Research Communications
SN - 0006-291X
IS - 2
ER -