LBF20207PG27: Difference between revisions

No edit summary
No edit summary
 
(17 intermediate revisions by the same user not shown)
Line 1: Line 1:
{{Lipid/Header}}
{{Hierarchy|{{PAGENAME}}}}
{{Hierarchy|{{PAGENAME}}}}


Line 4: Line 6:
|LipidBank=XPR1601
|LipidBank=XPR1601
|LipidMaps=LMFA03010009
|LipidMaps=LMFA03010009
|SysName=7- [ 2 (R) - (3 (S) -Hydroperoxy-1 (E) -octenyl) -1 (R) ,4 (S) -5,6-dioxabicyclo [ 2.2.1 ] -heptan-3 (R) -yl ] -5 (Z) -heptenoic acid
|SysName=7- [2R- (3S -Hydroxy-trans-1-octenyl) -(1R,4S) -5,6-dioxabicyclo [ 2.2.1 ] -heptan-3R-yl] -cis-5-heptenoic acid
|Common Name=&&PROSTAGLANDIN G_2&&7- [ 2 (R) - (3 (S) -Hydroperoxy-1 (E) -octenyl) -1 (R) ,4 (S) -5,6-dioxabicyclo [ 2.2.1 ] -heptan-3 (R) -yl ] -5 (Z) -heptenoic acid&&
|Common Name=&&Prostaglandin G_2&&7- [ 2R- (3S -Hydroxy-1-(E)-octenyl) -(1R,4S) -5,6-dioxabicyclo [ 2.2.1 ] -heptan-3R-yl ] -5(Z)-heptenoic acid&&
|NMR Spectra=<SUP><FONT SIZE=-1>1</FONT></SUP><SUP><FONT SIZE=-1>3</FONT></SUP>C-NMR : <FONT FACE="Symbol">d</FONT> 84.6(C15) [[Reference:Porter_NA:Byers_JD:Ali_AE:Eling_TE:,J. Am. Chem. Soc.,1980,102,1183|{{RelationTable/GetFirstAuthor|Reference:Porter_NA:Byers_JD:Ali_AE:Eling_TE:,J. Am. Chem. Soc.,1980,102,1183}}]]
|NMR Spectra=^{13}C-NMR :  delta  84.6(C15) [[Reference:Porter_NA:Byers_JD:Ali_AE:Eling_TE:,J. Am. Chem. Soc.,1980,102,1183|{{RelationTable/GetFirstAuthor|Reference:Porter_NA:Byers_JD:Ali_AE:Eling_TE:,J. Am. Chem. Soc.,1980,102,1183}}]]
|Source=Prostaglandin G2 is produced by bis-dioxygenation and cyclization of arachidonic acid as an intermediate for the biosyntheses of various prostaglandins and thromboxanes. The responsible enzyme is prostaglandin endoperoxide synthase usually referred to as fatty acid cyclooxygenase, and distributed in various animal tissues [[Reference:Pace-Asciak_CR:Smith_WL:,The_Enzymes,1983,16,543|{{RelationTable/GetFirstAuthor|Reference:Pace-Asciak_CR:Smith_WL:,The_Enzymes,1983,16,543}}]] <!--0019-->.
|Chemical Synthesis=[[Reference:Porter_NA:Byers_JD:Ali_AE:Eling_TE:,J. Am. Chem. Soc.,1980,102,1183|{{RelationTable/GetFirstAuthor|Reference:Porter_NA:Byers_JD:Ali_AE:Eling_TE:,J. Am. Chem. Soc.,1980,102,1183}}]] {{Image200|LBF20207PG27FT0001.gif}}
|Metabolism=Prostaglandin endoperoxide synthase is a bifunctional enzyme with an oxygenase activity (fatty acid cyclooxygenase) producing prostaglandin G2 from arachidonic acid and a peroxidase activity (prostagladnin hydroperoxidase) converting prostaglandin G2 to prostaglandin H2 <!--0019-->. The enzyme is usually referred to briefly as cyclooxygenase. There are two isozymes of the enzyme. Cyclooxygenase-1 is a constitutive enzyme expressed in most mammalian cells, while cyclooxygenase-2 is a product of immediate early gene and is induced rapidly and transiently in certain types of cell by various bioactive compounds [[Reference:Smith_WL:Garavito_RM:DeWitt_DL:,J. Biol. Chem.,1996,271,33157|{{RelationTable/GetFirstAuthor|Reference:Smith_WL:Garavito_RM:DeWitt_DL:,J. Biol. Chem.,1996,271,33157}}]][[Reference:Herschman_HR:,Biochim._Biophys._Acta,1996,1299,125|{{RelationTable/GetFirstAuthor|Reference:Herschman_HR:,Biochim._Biophys._Acta,1996,1299,125}}]]
|Symbol=PGG2
|Biological Activity=Prostaglandin G2 is a metabolic intermediate, but the compound as such has biological activities of bronchoconstriction and vasoconstriction [[Reference:Moncada_S:Vane_JR:,Pharmacol. Rev.,1978,30,293|{{RelationTable/GetFirstAuthor|Reference:Moncada_S:Vane_JR:,Pharmacol. Rev.,1978,30,293}}]][[Reference:Chijimatsu_Y:Nguyen_TV:Said_SI:,Prostaglandins,1977,13,909|{{RelationTable/GetFirstAuthor|Reference:Chijimatsu_Y:Nguyen_TV:Said_SI:,Prostaglandins,1977,13,909}}]].
|Genetic Information=cDNA and genomic DNA each for cyclooxygenas-1 and 2 were cloned [[Reference:Funk_CD:,Prog Nucleic Acid Res Mol Biol.,1993,45,67|{{RelationTable/GetFirstAuthor|Reference:Funk_CD:,Prog Nucleic Acid Res Mol Biol.,1993,45,67}}]].
|Note=Stability:unstable in water around neutrality with a half life of about 5 min at 37°C and decomposes to PGE2, PGD2, PGF2 and 12L-hydroxy-5,8,10-heptadecatrienoic acid[[Reference:Nugteren_DH:Hazelhof_E:,Biochim. Biophys. Acta,1973,326,448|{{RelationTable/GetFirstAuthor|Reference:Nugteren_DH:Hazelhof_E:,Biochim. Biophys. Acta,1973,326,448}}]].
}}
}}
{{Lipid/Footer}}

Latest revision as of 08:31, 21 October 2010

LipidBank Top
(トップ)
Fatty acid
(脂肪酸)
Glycerolipid
(グリセロ脂質)
Sphingolipid
(スフィンゴ脂質)
Journals
(雑誌一覧)
How to edit
(ページの書き方)


Upper classes: LB LBF



Prostaglandin G2
LBF20207PG27.png
Structural Information
7- [2R- (3S -Hydroxy-trans-1-octenyl) -(1R,4S) -5,6-dioxabicyclo [ 2.2.1 ] -heptan-3R-yl] -cis-5-heptenoic acid
  • Prostaglandin G2
  • 7- [ 2R- (3S -Hydroxy-1-(E)-octenyl) -(1R,4S) -5,6-dioxabicyclo [ 2.2.1 ] -heptan-3R-yl ] -5(Z)-heptenoic acid
PGG2
Formula C20H32O6
Exact Mass 368.219888756
Average Mass 368.46448
SMILES C(CC[C@@H](OO)C=C[C@@H]([C@H]21)[C@@H](CC=CCCCC(O)=O)[C@@H](OO2)C1)CC
Physicochemical Information
Prostaglandin G2 is produced by bis-dioxygenation and cyclization of arachidonic acid as an intermediate for the biosyntheses of various prostaglandins and thromboxanes. The responsible enzyme is prostaglandin endoperoxide synthase usually referred to as fatty acid cyclooxygenase, and distributed in various animal tissues Pace-Asciak_CR et al. .
Porter_NA et al.
LBF20207PG27FT0001.gif
Prostaglandin endoperoxide synthase is a bifunctional enzyme with an oxygenase activity (fatty acid cyclooxygenase) producing prostaglandin G2 from arachidonic acid and a peroxidase activity (prostagladnin hydroperoxidase) converting prostaglandin G2 to prostaglandin H2 . The enzyme is usually referred to briefly as cyclooxygenase. There are two isozymes of the enzyme. Cyclooxygenase-1 is a constitutive enzyme expressed in most mammalian cells, while cyclooxygenase-2 is a product of immediate early gene and is induced rapidly and transiently in certain types of cell by various bioactive compounds Smith_WL et al. Herschman_HR
Prostaglandin G2 is a metabolic intermediate, but the compound as such has biological activities of bronchoconstriction and vasoconstriction Moncada_S et al. Chijimatsu_Y et al..
cDNA and genomic DNA each for cyclooxygenas-1 and 2 were cloned Funk_CD .
Stability:unstable in water around neutrality with a half life of about 5 min at 37°C and decomposes to PGE2, PGD2, PGF2 and 12L-hydroxy-5,8,10-heptadecatrienoic acid Nugteren_DH et al..
Spectral Information
Mass Spectra
UV Spectra
IR Spectra
NMR Spectra 13C-NMR : δ 84.6(C15) Porter_NA et al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20207PG27 See above. Chijimatsu_Y et al. 1977
n.a. LBF20207PG27 See above. Funk_CD 1993
n.a. LBF20207PG27 See above. Herschman_HR 1996
n.a. LBF20207PG27 See above. Moncada_S et al. 1978
n.a. LBF20207PG27 See above. Nugteren_DH et al. 1973
n.a. LBF20207PG27 See above. Pace-Asciak_CR et al. 1983
n.a. LBF20207PG27 See above. Porter_NA et al. 1980
n.a. LBF20207PG27 See above. Smith_WL et al. 1996