LBF20406LT01: Difference between revisions

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|SysName=5 (S) ,6 (S) -Epoxyeicosa-7 (E) ,9 (E) ,11 (Z) ,14 (Z) -tetraenoic acid
|SysName=5 (S) ,6 (S) -Epoxyeicosa-7 (E) ,9 (E) ,11 (Z) ,14 (Z) -tetraenoic acid
|Common Name=&&LEUKOTRIENE A4&&5 (S) ,6 (S) -Epoxyeicosa-7 (E) ,9 (E) ,11 (Z) ,14 (Z) -tetraenoic acid&&
|Common Name=&&LEUKOTRIENE A4&&5 (S) ,6 (S) -Epoxyeicosa-7 (E) ,9 (E) ,11 (Z) ,14 (Z) -tetraenoic acid&&
|Reflactive=[<FONT FACE="Symbol">a</FONT>]X<sub>D</sub><sup>25</sup>=-21.9°(C=0.32,CYCLOHEXANE) [[Reference:Corey_EJ:Clark_DA:Goto_G:Marfat_A:Mioskowski_C:Samuelsson_B:Hammarstroem_S:,J. Am. Chem. Soc.,1980,102,1436|{{RelationTable/GetFirstAuthor|Reference:Corey_EJ:Clark_DA:Goto_G:Marfat_A:Mioskowski_C:Samuelsson_B:Hammarstroem_S:,J. Am. Chem. Soc.,1980,102,1436}}]]
|Optical=[<FONT FACE="Symbol">a</FONT>]X<sub>D</sub><sup>25</sup>=-21.9°(C=0.32,CYCLOHEXANE) [[Reference:Corey_EJ:Clark_DA:Goto_G:Marfat_A:Mioskowski_C:Samuelsson_B:Hammarstroem_S:,J. Am. Chem. Soc.,1980,102,1436|{{RelationTable/GetFirstAuthor|Reference:Corey_EJ:Clark_DA:Goto_G:Marfat_A:Mioskowski_C:Samuelsson_B:Hammarstroem_S:,J. Am. Chem. Soc.,1980,102,1436}}]]
|Solubility=SOL. IN CYCLOHEXANE,METHANOL[[Reference:Corey_EJ:Clark_DA:Goto_G:Marfat_A:Mioskowski_C:Samuelsson_B:Hammarstroem_S:,J. Am. Chem. Soc.,1980,102,1436|{{RelationTable/GetFirstAuthor|Reference:Corey_EJ:Clark_DA:Goto_G:Marfat_A:Mioskowski_C:Samuelsson_B:Hammarstroem_S:,J. Am. Chem. Soc.,1980,102,1436}}]]. STABILITIES : to decompose to 5,12-DIHYDROXY-6,8,10,14-EICOSATETRAENOIC ACID and 5,6-DIHYDROXY-7,9,11,14-EICOSATETRAENOIC ACID under neutral aqueous solution at 37°C with one minite of half-life[[Reference:Borgeat_P:Samuelsson_B:,Proc. Natl. Acad. Sci. U. S. A.,1979,76,3213|{{RelationTable/GetFirstAuthor|Reference:Borgeat_P:Samuelsson_B:,Proc. Natl. Acad. Sci. U. S. A.,1979,76,3213}}]].
|Solubility=SOL. IN CYCLOHEXANE,METHANOL[[Reference:Corey_EJ:Clark_DA:Goto_G:Marfat_A:Mioskowski_C:Samuelsson_B:Hammarstroem_S:,J. Am. Chem. Soc.,1980,102,1436|{{RelationTable/GetFirstAuthor|Reference:Corey_EJ:Clark_DA:Goto_G:Marfat_A:Mioskowski_C:Samuelsson_B:Hammarstroem_S:,J. Am. Chem. Soc.,1980,102,1436}}]]. STABILITIES : to decompose to 5,12-DIHYDROXY-6,8,10,14-EICOSATETRAENOIC ACID and 5,6-DIHYDROXY-7,9,11,14-EICOSATETRAENOIC ACID under neutral aqueous solution at 37°C with one minite of half-life[[Reference:Borgeat_P:Samuelsson_B:,Proc. Natl. Acad. Sci. U. S. A.,1979,76,3213|{{RelationTable/GetFirstAuthor|Reference:Borgeat_P:Samuelsson_B:,Proc. Natl. Acad. Sci. U. S. A.,1979,76,3213}}]].
|Mass Spectra=METHYL ESTER ; 332(M<SUP><FONT SIZE=-1>+</FONT></SUP>), 316, 300, 221, 189, 181, 129, 101 [[Reference:Mckay_SW:Mallen_DNB:Shrubasall_PR:Smith_JM:Baker_SR:Jamieson_WB:Ross_WJ:Morgan_SE:Rackham_DM:,J. Chromatogr. A,1981,214,249|{{RelationTable/GetFirstAuthor|Reference:Mckay_SW:Mallen_DNB:Shrubasall_PR:Smith_JM:Baker_SR:Jamieson_WB:Ross_WJ:Morgan_SE:Rackham_DM:,J. Chromatogr. A,1981,214,249}}]]
|Mass Spectra=METHYL ESTER ; 332(M<SUP><FONT SIZE=-1>+</FONT></SUP>), 316, 300, 221, 189, 181, 129, 101 [[Reference:Mckay_SW:Mallen_DNB:Shrubasall_PR:Smith_JM:Baker_SR:Jamieson_WB:Ross_WJ:Morgan_SE:Rackham_DM:,J. Chromatogr. A,1981,214,249|{{RelationTable/GetFirstAuthor|Reference:Mckay_SW:Mallen_DNB:Shrubasall_PR:Smith_JM:Baker_SR:Jamieson_WB:Ross_WJ:Morgan_SE:Rackham_DM:,J. Chromatogr. A,1981,214,249}}]]
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|Chemical Synthesis=[[Reference:Corey_EJ:Arai_Y:Mioskowski_C:,J. Am. Chem. Soc.,1979,101,6748|{{RelationTable/GetFirstAuthor|Reference:Corey_EJ:Arai_Y:Mioskowski_C:,J. Am. Chem. Soc.,1979,101,6748}}]] {{Image200|LBF20406LT01FT0001.gif}}
|Chemical Synthesis=[[Reference:Corey_EJ:Arai_Y:Mioskowski_C:,J. Am. Chem. Soc.,1979,101,6748|{{RelationTable/GetFirstAuthor|Reference:Corey_EJ:Arai_Y:Mioskowski_C:,J. Am. Chem. Soc.,1979,101,6748}}]] {{Image200|LBF20406LT01FT0001.gif}}
|Metabolism=Arachidonate 5-lipoxygenase is a bifunctional enzyme with a 5-oxygenase activity converting arachidonic acid to 5-hydroperoxy-6,8,11,14-eicosatetraenoic acid and a leukotriene A synthase activity converting the 5-hydroperoxy acid to leukotriene A4. The same enzyme produces leukotriene A4 from arachidonic acid via 5-hydroperoxy acid [[Reference:Ford-Hutchinson_AW:Gresser_M:Young_RN:,Annu. Rev. Biochem.,1994,63,383|{{RelationTable/GetFirstAuthor|Reference:Ford-Hutchinson_AW:Gresser_M:Young_RN:,Annu. Rev. Biochem.,1994,63,383}}]]. The produced leukotriene A4 ia converted either to leukotriene B4 or to leukotriene C4 [[Reference:Hammarstrom_S:,Annu. Rev. Biochem.,1983,52,355|{{RelationTable/GetFirstAuthor|Reference:Hammarstrom_S:,Annu. Rev. Biochem.,1983,52,355}}]].
|Metabolism=Arachidonate 5-lipoxygenase is a bifunctional enzyme with a 5-oxygenase activity converting arachidonic acid to 5-hydroperoxy-6,8,11,14-eicosatetraenoic acid and a leukotriene A synthase activity converting the 5-hydroperoxy acid to leukotriene A4. The same enzyme produces leukotriene A4 from arachidonic acid via 5-hydroperoxy acid [[Reference:Ford-Hutchinson_AW:Gresser_M:Young_RN:,Annu. Rev. Biochem.,1994,63,383|{{RelationTable/GetFirstAuthor|Reference:Ford-Hutchinson_AW:Gresser_M:Young_RN:,Annu. Rev. Biochem.,1994,63,383}}]]. The produced leukotriene A4 ia converted either to leukotriene B4 or to leukotriene C4 [[Reference:Hammarstrom_S:,Annu. Rev. Biochem.,1983,52,355|{{RelationTable/GetFirstAuthor|Reference:Hammarstrom_S:,Annu. Rev. Biochem.,1983,52,355}}]].
|Symbol=LTA4
|Biological Activity=Leukotriene A4 as such is biologically less active than its active metabolites, leukotrienes B4 and C4. For example, leukotriene A4 is at least two orders of magnitude less potent than leukotrienes C4, D4 and E4 in contraction of guinea pig lung strips [[Reference:Hammarstrom_S:,Annu. Rev. Biochem.,1983,52,355|{{RelationTable/GetFirstAuthor|Reference:Hammarstrom_S:,Annu. Rev. Biochem.,1983,52,355}}]].
}}
}}


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Revision as of 21:00, 6 January 2010

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Upper classes: LB LBF



IDs and Links
LipidBank XPR3001
LipidMaps LMFA03020023
CAS
KEGG {{{KEGG}}}
KNApSAcK {{{KNApSAcK}}}
mol LBF20406LT01
LEUKOTRIENE A4
LBF20406LT01.png
Structural Information
5 (S) ,6 (S) -Epoxyeicosa-7 (E) ,9 (E) ,11 (Z) ,14 (Z) -tetraenoic acid
  • LEUKOTRIENE A4
  • 5 (S) ,6 (S) -Epoxyeicosa-7 (E) ,9 (E) ,11 (Z) ,14 (Z) -tetraenoic acid
 LTA4
Formula C20H30O3
Exact Mass 318.21949482599996
Average Mass 318.4504
SMILES C(CC=CCC=CC=CC=C[C@@H](O1)[C@@H]1CCCC(O)=O)CCC
Physicochemical Information
[a]XD25=-21.9°(C=0.32,CYCLOHEXANE) Corey_EJ et al.
SOL. IN CYCLOHEXANE,METHANOL Corey_EJ et al.. STABILITIES : to decompose to 5,12-DIHYDROXY-6,8,10,14-EICOSATETRAENOIC ACID and 5,6-DIHYDROXY-7,9,11,14-EICOSATETRAENOIC ACID under neutral aqueous solution at 37°C with one minite of half-life BorgeatPet al..
Leukotriene A4 is produced as an intermediate for the biosyntheses of leukotrienes B4 and C4 in polymorphonuclear leukocytes, mast cells and macrophages of various animal species Hammarstrom_S .
Corey_EJ et al.
LBF20406LT01FT0001.gif
 Arachidonate 5-lipoxygenase is a bifunctional enzyme with a 5-oxygenase activity converting arachidonic acid to 5-hydroperoxy-6,8,11,14-eicosatetraenoic acid and a leukotriene A synthase activity converting the 5-hydroperoxy acid to leukotriene A4. The same enzyme produces leukotriene A4 from arachidonic acid via 5-hydroperoxy acid Ford-Hutchinson_AW et al.. The produced leukotriene A4 ia converted either to leukotriene B4 or to leukotriene C4 Hammarstrom_S .
Leukotriene A4 as such is biologically less active than its active metabolites, leukotrienes B4 and C4. For example, leukotriene A4 is at least two orders of magnitude less potent than leukotrienes C4, D4 and E4 in contraction of guinea pig lung strips Hammarstrom_S .
Spectral Information
Mass Spectra METHYL ESTER ; 332(M+), 316, 300, 221, 189, 181, 129, 101 Mckay_SW et al.
UV Spectra METHYL ESTER ; l MeOHmax = 269(e 30,500), 278(e 40,000), 287(e 34,400) nm Corey_EJ et al.
IR Spectra
NMR Spectra
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20406LT01 See above. Borgeat_P et al. 1979
n.a. LBF20406LT01 See above. Corey_EJ et al. 1979
n.a. LBF20406LT01 See above. Corey_EJ et al. 1980
n.a. LBF20406LT01 See above. Ford-Hutchinson_AW et al. 1994
n.a. LBF20406LT01 See above. Funk_CD 1993
n.a. LBF20406LT01 See above. Hammarstrom_S 1983
n.a. LBF20406LT01 See above. Mckay_SW et al. 1981
n.a. LBF20406LT01 See above. Samuelsson_B et al. 1982


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