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|IR Spectra=NEAT : 3320, 2640, 1710, 1295, 1260, 1245, 1120, 1080, 1055, 1025, 975cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP> [[Reference:Pike_J_E:Lincoln_FH:Schneider_WP:,J. Org. Chem.,1969,34,3552|{{RelationTable/GetFirstAuthor|Reference:Pike_J_E:Lincoln_FH:Schneider_WP:,J. Org. Chem.,1969,34,3552}}]]
|IR Spectra=NEAT : 3320, 2640, 1710, 1295, 1260, 1245, 1120, 1080, 1055, 1025, 975cm<SUP><FONT SIZE=-1>-</FONT></SUP><SUP><FONT SIZE=-1>1</FONT></SUP> [[Reference:Pike_J_E:Lincoln_FH:Schneider_WP:,J. Org. Chem.,1969,34,3552|{{RelationTable/GetFirstAuthor|Reference:Pike_J_E:Lincoln_FH:Schneider_WP:,J. Org. Chem.,1969,34,3552}}]]
|NMR Spectra=<SUP><FONT SIZE=-1>1</FONT></SUP>H-NMR(d<SUB><FONT SIZE=-1>6</FONT></SUB>-ACETONE) : <FONT FACE="Symbol">d</FONT> 5.48(m, 4H), 4.05(m, 3H), 0.9(t, 3H, 20-CH3) [[Reference:Pike_J_E:Lincoln_FH:Schneider_WP:,J. Org. Chem.,1969,34,3552|{{RelationTable/GetFirstAuthor|Reference:Pike_J_E:Lincoln_FH:Schneider_WP:,J. Org. Chem.,1969,34,3552}}]]. <SUP><FONT SIZE=-1>1</FONT></SUP><SUP><FONT SIZE=-1>3</FONT></SUP>C-NMR : 176.6(C1), 135.0(C14), 132.8(C5), 129.1(C13 or C6), 128.9(C6 or C13), 77.2(C11), 72.9(C15), 71.8(C9), 55.0(C12), 49.9(C8), 42,6(C10), 36.8(C16), 33.2(C2), 31,5(C18), 26.3(C4), 25.1(C7), 25.1(C17), 24.5 [[Reference:Lukacs_G:Piriou_F:Gero_SD:,Tetrah. Lett.,1973,,515|{{RelationTable/GetFirstAuthor|Reference:Lukacs_G:Piriou_F:Gero_SD:,Tetrah. Lett.,1973,,515}}]]
|NMR Spectra=<SUP><FONT SIZE=-1>1</FONT></SUP>H-NMR(d<SUB><FONT SIZE=-1>6</FONT></SUB>-ACETONE) : <FONT FACE="Symbol">d</FONT> 5.48(m, 4H), 4.05(m, 3H), 0.9(t, 3H, 20-CH3) [[Reference:Pike_J_E:Lincoln_FH:Schneider_WP:,J. Org. Chem.,1969,34,3552|{{RelationTable/GetFirstAuthor|Reference:Pike_J_E:Lincoln_FH:Schneider_WP:,J. Org. Chem.,1969,34,3552}}]]. <SUP><FONT SIZE=-1>1</FONT></SUP><SUP><FONT SIZE=-1>3</FONT></SUP>C-NMR : 176.6(C1), 135.0(C14), 132.8(C5), 129.1(C13 or C6), 128.9(C6 or C13), 77.2(C11), 72.9(C15), 71.8(C9), 55.0(C12), 49.9(C8), 42,6(C10), 36.8(C16), 33.2(C2), 31,5(C18), 26.3(C4), 25.1(C7), 25.1(C17), 24.5 [[Reference:Lukacs_G:Piriou_F:Gero_SD:,Tetrah. Lett.,1973,,515|{{RelationTable/GetFirstAuthor|Reference:Lukacs_G:Piriou_F:Gero_SD:,Tetrah. Lett.,1973,,515}}]]
|Source=Prostaglandin F2<FONT FACE="Symbol">a</FONT> was found to be accummulating in human semen in an amount of about 2 microgram per ml [[Reference:Bergstrom_S:,Science,1967,157,382|{{RelationTable/GetFirstAuthor|Reference:Bergstrom_S:,Science,1967,157,382}}]];>. In most animal tissues prostanoids are synthesized enzymatically de novo upon physiological and pathological stimulations, and this is also the case of prostaglandin F2<FONT FACE="Symbol">a</FONT>.
|Source=Prostaglandin F2<FONT FACE="Symbol">a</FONT> was found to be accummulating in human semen in an amount of about 2 microgram per ml [[Reference:Bergstrom_S:,Science,1967,157,382|{{RelationTable/GetFirstAuthor|Reference:Bergstrom_S:,Science,1967,157,382}}]]. In most animal tissues prostanoids are synthesized enzymatically de novo upon physiological and pathological stimulations, and this is also the case of prostaglandin F2<FONT FACE="Symbol">a</FONT>.
|Chemical Synthesis=[[Reference:Corey_EJ:Schaaf_TK:Huber_W:Koelliker_U:Weinshenker_NM:,J. Am. Chem. Soc.,1970,92,397|{{RelationTable/GetFirstAuthor|Reference:Corey_EJ:Schaaf_TK:Huber_W:Koelliker_U:Weinshenker_NM:,J. Am. Chem. Soc.,1970,92,397}}]];> {{Image200|LBF20207PG25FT0001.gif}}
|Chemical Synthesis=[[Reference:Corey_EJ:Schaaf_TK:Huber_W:Koelliker_U:Weinshenker_NM:,J. Am. Chem. Soc.,1970,92,397|{{RelationTable/GetFirstAuthor|Reference:Corey_EJ:Schaaf_TK:Huber_W:Koelliker_U:Weinshenker_NM:,J. Am. Chem. Soc.,1970,92,397}}]] {{Image200|LBF20207PG25FT0001.gif}}
|Metabolism=Prostaglandin F synthase reduces 9,11-endoperoxide of prostaglandin H2 requiring NADPH, and produces prostaglandin F2<FONT FACE="Symbol">a</FONT>. The same enzyme also reduces 9-keto group of prostaglandin D2 producing 11<FONT FACE="Symbol">b</FONT>-prostaglandin F2 [[Reference:Urade_Y:Watanabe_K:Hayaishi_O:,J. Lipid Mediat. Cell Signal.,1995,12,257|{{RelationTable/GetFirstAuthor|Reference:Urade_Y:Watanabe_K:Hayaishi_O:,J. Lipid Mediat. Cell Signal.,1995,12,257}}]];>.
|Metabolism=Prostaglandin F synthase reduces 9,11-endoperoxide of prostaglandin H2 requiring NADPH, and produces prostaglandin F2<FONT FACE="Symbol">a</FONT>. The same enzyme also reduces 9-keto group of prostaglandin D2 producing 11<FONT FACE="Symbol">b</FONT>-prostaglandin F2 [[Reference:Urade_Y:Watanabe_K:Hayaishi_O:,J. Lipid Mediat. Cell Signal.,1995,12,257|{{RelationTable/GetFirstAuthor|Reference:Urade_Y:Watanabe_K:Hayaishi_O:,J. Lipid Mediat. Cell Signal.,1995,12,257}}]].
}}
}}


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Revision as of 11:55, 25 November 2009

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Upper classes: LB LBF



PROSTAGLANDIN F_2α
LBF20207PG25.png
Structural Information
7- [ 3 (R) ,5 (S) -Dihydroxy-2 (R) - (3 (S) -hydroxy-1 (E) -octenylcyclopentan-1 (R) -yl ] -5 (Z) -heptenoic acid
  • PROSTAGLANDIN F_2α
  • 7- [ 3 (R) ,5 (S) -Dihydroxy-2 (R) - (3 (S) -hydroxy-1 (E) -octenylcyclopentan-1 (R) -yl ] -5 (Z) -heptenoic acid
Formula C20H34O5
Exact Mass 354.240624198
Average Mass 354.48096000000004
SMILES C(CC[C@@H](O)C=C[C@H]([C@H]1CC=CCCCC(O)=O)[C@@H](C[C@@H]1O)O)CC
Physicochemical Information
25-35°C Bundy_GL et al.
ETHYL ACETATE, ACETONE, DIETHYLETHER Pike_JEet al.. STABILITIES: to be stable under neutral and basic conditions Karim_SM et al.
Prostaglandin F2a was found to be accummulating in human semen in an amount of about 2 microgram per ml Bergstrom_S . In most animal tissues prostanoids are synthesized enzymatically de novo upon physiological and pathological stimulations, and this is also the case of prostaglandin F2a.
Corey_EJ et al.
LBF20207PG25FT0001.gif
Prostaglandin F synthase reduces 9,11-endoperoxide of prostaglandin H2 requiring NADPH, and produces prostaglandin F2a. The same enzyme also reduces 9-keto group of prostaglandin D2 producing 11b-prostaglandin F2 Urade_Y et al..
Spectral Information
Mass Spectra 354(M+), 336, 318, 292, 274, 264(100), 247, 229, 191, 177, 165, 137, 99, 81, 67 HorvathG
UV Spectra
IR Spectra NEAT : 3320, 2640, 1710, 1295, 1260, 1245, 1120, 1080, 1055, 1025, 975cm-1 Pike_JEet al.
NMR Spectra 1H-NMR(d6-ACETONE) : d 5.48(m, 4H), 4.05(m, 3H), 0.9(t, 3H, 20-CH3) Pike_JEet al.. 13C-NMR : 176.6(C1), 135.0(C14), 132.8(C5), 129.1(C13 or C6), 128.9(C6 or C13), 77.2(C11), 72.9(C15), 71.8(C9), 55.0(C12), 49.9(C8), 42,6(C10), 36.8(C16), 33.2(C2), 31,5(C18), 26.3(C4), 25.1(C7), 25.1(C17), 24.5 LukacsGet al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20207PG25 See above. Bergstrom_S 1967
n.a. LBF20207PG25 See above. Bergstrom_S et al. 1968
n.a. LBF20207PG25 See above. Bundy_GL et al. 1972
n.a. LBF20207PG25 See above. Corey_EJ et al. 1970
n.a. LBF20207PG25 See above. Horvath_G 1976
n.a. LBF20207PG25 See above. Karim_SM et al. 1968
n.a. LBF20207PG25 See above. Lukacs_G et al. 1973
n.a. LBF20207PG25 See above. Negishi_M et al. 1995
n.a. LBF20207PG25 See above. Pike_JE et al. 1969
n.a. LBF20207PG25 See above. Urade_Y et al. 1995