Prostaglandin G2

Last updated
Prostaglandin G2
Prostaglandin G2.svg
Names
IUPAC name
(5Z)-7-{(1R,4S,5R,6R)-6-[(1E,3S)-3-Hydroperoxy-1-octen-1-yl]-2,3-dioxabicyclo[2.2.1]hept-5-yl}-5-heptenoic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
EC Number
  • 200-662-2
KEGG
PubChem CID
UNII
  • InChI=1S/C20H32O6/c1-2-3-6-9-15(24-23)12-13-17-16(18-14-19(17)26-25-18)10-7-4-5-8-11-20(21)22/h4,7,12-13,15-19,23H,2-3,5-6,8-11,14H2,1H3,(H,21,22)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1
    Key: SGUKUZOVHSFKPH-YNNPMVKQSA-N
  • InChI=1/C20H32O6/c1-2-3-6-9-15(24-23)12-13-17-16(18-14-19(17)26-25-18)10-7-4-5-8-11-20(21)22/h4,7,12-13,15-19,23H,2-3,5-6,8-11,14H2,1H3,(H,21,22)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1
    Key: SGUKUZOVHSFKPH-YNNPMVKQBO
  • CCCCC[C@@H](/C=C/[C@H]1[C@H]2C[C@@H]([C@@H]1C/C=C\CCCC(=O)O)OO2)OO
Properties
C20H32O6
Molar mass 368.470 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Prostaglandin G2 (PGG2) is an organic peroxide belonging to the family of prostaglandins. [1] The compound has been isolated as a solid, although it is usually used in vivo. It quickly converts into prostaglandin H2, a process catalyzed by the enzyme cyclooxygenase (COX).

Prostaglandin G2 is produced from the fatty acid arachidonic acid. The reaction, a double oxygenation, requires the enzyme COX, which inserts two molecules of O2 into the C-H bonds of the substrate acid. [2] [1] [3]

References

  1. 1 2 Wilfred van der Donk; Tsai Ah-Lim; Kulmacz Richard J. (2002). "The cyclooxygenase reaction mechanism". Biochemistry. 41 (52): 15451–8. doi:10.1021/bi026938h. PMID   12501173.
  2. ↑ Rouzer, Carol A.; Marnett, Lawrence J. (2003). "Mechanism of Free Radical Oxygenation of Polyunsaturated Fatty Acids by Cyclooxygenases". Chemical Reviews. 103 (6): 2239–2304. doi:10.1021/cr000068x. PMID   12797830.
  3. ↑ "Prostaglandin G2". Santa cruz biotechnology, inc. Retrieved 27 April 2015.



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