Chemistry:Prostaglandin H2
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| Other names
PGH2, Endoperoxide H2, Prostaglandin R2
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3D model (JSmol)
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| MeSH | Prostaglandin+H2 |
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| Properties | |
| C20H32O5 | |
| Molar mass | 352.465 g/mol |
| Density | 1.129 ± 0.06 g/mL |
| Boiling point | 490 ± 40.0 °C |
| 0.034 g/L | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
 verify (what is   ?)
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| Infobox references | |
Prostaglandin H2 is a type of prostaglandin and a precursor for many other biologically significant molecules. It is synthesized from arachidonic acid in a reaction catalyzed by a cyclooxygenase enzyme.[2] The conversion from Arachidonic acid to Prostaglandin H2 is a two step process. First, COX-1 catalyzes the addition of two free oxygens to form the 1,2-Dioxane bridge and a peroxide functional group to form Prostaglandin G2.[3] Second, COX-2 reduces the peroxide functional group to a Secondary alcohol, forming Prostaglandin H2. Other peroxidases like Hydroquinone have been observed to reduce PGG2 to PGH2.[4] PGH2 is unstable at room temperature, with a half life of 90-100 seconds,[1] so it is often converted into a different prostaglandin.
It is acted upon by:
- Prostacyclin synthase to create prostacyclin
- Thromboxane-A synthase to create thromboxane A2 and 12-(S)-hydroxy-5Z,8E,10E-heptadecatrienoic acid (HHT) (see 12-Hydroxyheptadecatrienoic acid)
- Prostaglandin D2 synthase to create prostaglandin D2
- Prostaglandin E synthase to create prostaglandin E2
It rearranges non-enzymatically to:
- A mixture of 12-(S)-hydroxy-5Z,8E,10E-heptadecatrienoic acid (HHT) and 12-(S)-hydroxy-5Z,8Z,10E-heptadecatrienoic acid (see 12-Hydroxyheptadecatrienoic acid)
Use of prostaglandin H2:
- regulating the constriction and dilation of blood vessels
- stimulating platelet aggregation
- binds to Thromboxane receptor on platelets' cell membranes to trigger platelet migration and adhesion to other platelets.[5]
Effects of Aspirin on prostaglandin H2:
- Aspirin has been hypothesized to block the conversion of arachidonic acid to prostaglandin
References
- ↑ 1.0 1.1 Wishart, David S.; Djombou Feunang, Yannick; Marcu, Ana; Guo, An Chi; Liang, Kevin; Vázquez Fresno, Rosa; Sajed, Tanvir; Johnson, Daniel et al.. "Showing metabocard for Prostaglandin H2 (HMDB0001381)". http://www.hmdb.ca/metabolites/HMDB0001381.
- ↑ "The cyclooxygenase reaction mechanism". Biochemistry 41 (52): 15451–8. December 2002. doi:10.1021/bi026938h. PMID 12501173.
- ↑ Salomon, Robert G.; Miller, Donald B.; Zagorski, Michael G.; Coughlin, Daniel J. (October 1984). "Prostaglandin endoperoxides. 14. Solvent-induced fragmentation of prostaglandin endoperoxides. New aldehyde products from PGH2 and a novel intramolecular 1,2-hydride shift during endoperoxide fragmentation in aqueous solution". Journal of the American Chemical Society 106 (20): 6049–6060. doi:10.1021/ja00332a049. ISSN 0002-7863.
- ↑ "Human cyclooxygenase-2 cDNA". Proceedings of the National Academy of Sciences of the United States of America 89 (16): 7384–8. August 1992. doi:10.1073/pnas.89.16.7384. PMID 1380156. Bibcode: 1992PNAS...89.7384H.
- ↑ "International Union of Basic and Clinical Pharmacology. LXXXIII: classification of prostanoid receptors, updating 15 years of progress". Pharmacological Reviews 63 (3): 471–538. September 2011. doi:10.1124/pr.110.003517. PMID 21752876.
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