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Eicosanoid


DATA No : XPR3001 INFORMANT : Shouzo Yamamoto

NAME : 5(S),6(S)-Epoxyeicosa-7(E),9(E),11(Z),14(Z)-tetraenoic acid

COMMON NAME: LEUKOTRIENE A4
SYMBOL: LTA4
FORMULA: C20H30O3 MOL.WT (average) : 318.450


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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 (Ref. 0022).
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]d-25=-21.9deg(C=0.32,CYCLOHEXANE) (Ref. 1024)

DENSITY:

SOLUBILITY:SOL. IN CYCLOHEXANE,METHANOL(Ref. 1024). 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 37degC with one minite of half-life(Ref. 1030).
SPECTRAL DATA
UV SPECTRA:METHYL ESTER ; l MeOHmax = 269(e 30,500), 278(e 40,000), 287(e 34,400) nm (Ref. 1031)

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:METHYL ESTER ; 332(M+), 316, 300, 221, 189, 181, 129, 101 (Ref. 1029)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
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 (Ref. 0022).
CHEMICAL SYNTHESIS
(Ref. 1031)
[Table 0001]
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 (Ref. 0025). The produced leukotriene A4 ia converted either to leukotriene B4 or to leukotriene C4 (Ref. 0022).
GENETIC INFORMATION
cDNA and genomic DNA for 5-lipoxygenase were cloned (Ref. 0007).
NOTE
Stability:unstable in water around neutrality with a half life of about 1 min at 37degC and decomposes to 5,12-dihydroxy-6,8,10,14-eicosatetraenoic acid and 5,6-dihydroxy-7,9,11,14-eicosatetraenoic acid(Ref. 0021)
REFERENCES
[0007]
AUTHOR:Funk, C.D.
TITLE:Molecular biology in the eicosanoid field . PubMed ID:8341804
JOURNAL:Progr. Nucleic Acid Res.
VOL:45 PAGE : 67 -98 (1993)
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[0021]
AUTHOR:Samuelsson, B., and Hammarstrom, S.
TITLE:Leukotrienes: a novel group of biologically active compounds PubMed ID:6293196
JOURNAL:Vitam Horm.
VOL:39 PAGE : 1-30 (1982)
[TOP]

[0022]
AUTHOR:Hammarstrom, S.
TITLE:Leukotrienes PubMed ID:6311078
JOURNAL:Annu Rev Biochem.
VOL:52 PAGE : 355-377 (1983)
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[0025]
AUTHOR:Ford-Hutchinson, A. W., Gresser, M., and Young, R. N.
TITLE:5-Lipoxygenase PubMed ID:7979243
JOURNAL:Annu Rev Biochem.
VOL:63 PAGE : 383-417 (1994)
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[1024]
AUTHOR:Corey,E.J., Clark,D.A., Goto,G., Marfat,A., Mioskowski,C., Samuelsson,B., and Hammarströ$m,S.
TITLE:Stereospecific Total Synthesis of a 'Slow Reacting Substance' of Anaphylaxis, Leucotriene C-1.
JOURNAL:J. Am. Chem. Soc.
VOL:102 PAGE : 1436 -1439 (1980)
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[1029]
AUTHOR:Mckay,S.W., Maller,O.N.B., Shrubasall,P.R., Smith,J.M., Baker,S.R., Jamieson,W.B., and Ross,W.J.
TITLE:Semi Preparative High Performance Liquid Chromatography and Spectroscopic Characterization of 8 Genometric Isomers of Leukotriene A Methyl Ester.
JOURNAL:J. Chromatogr.
VOL:214 PAGE : 249 -256 (1981)
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[1030]
AUTHOR:Borgeat,P., and Samuelsson,B.
TITLE:Arachidonic Acid Metabolism in Polymorphonuclear Leukocytes: Unstable Intermediate in Formation of Dihydroxy Acids. PubMed ID:290996
JOURNAL:Proc. Nat. Acad. Sci. USA
VOL:76 PAGE : 3213 -3217 (1979)
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[1031]
AUTHOR:Cory,E.J., Arai,Y., and Mioskowski,C.
TITLE:Total Synthesis of (pm)-5,6-Oxido-7,9-trans,11,14-cis-eicosapentaenoic Acid, a Possible Precursor of SRSA.
JOURNAL:J. Am. Che. Soc.
VOL:101 PAGE : 6748 -6749 (1979)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.