Back to HOME

Eicosanoid


DATA No : XPR6001 INFORMANT : Shouzo Yamamoto

NAME : 5(S)-Hydroperoxy-6,8,11,14-(E,Z,Z,Z)-eicosatetraenoic acid

COMMON NAME:
SYMBOL: 5(S)-HPETE
FORMULA: C20H32O4 MOL.WT (average) : 336.466


Download ChemDraw structure data
BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:DIETHYL ETHER (Ref. 1077). ETHYL ACETATE (Ref. 1078)
SPECTRAL DATA
UV SPECTRA: l MeOHmax = 230nm (Ref. 1076)

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS

METABOLISM
Arachidonic acid is oxygenated at the position 5 by the 5-oxygenase activity of arachidonate 5-lipoxygenase, and transformed to 5(S)-hydroperoxy-6,8,11,14-(E,Z,Z,Z)-eicosatetraenoic acid, which is further converted to leukotriene A4 by the same enzyme. Thus, the 5-hydroperoxy acid is an intermediate for leukotriene A4 synthesis (Ref. 0025).
GENETIC INFORMATION
cDNA and genomic DNA of 5-lipoxygenase were cloned (Ref. 0007).
NOTE

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)
[TOP]

[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)
[TOP]

[1076]
AUTHOR:Corey,E.J., Wright,S.W. and Matsuda,S.P.T.
TITLE:Stereochemistry and Mechanism of the Biosynthesis of Leukotriene A4 from 5(S)-Hydroxy-6(E),8,11,14(Z)-eicosatetraenoic Acid. Evidence for an Organoiron Intermediates.
JOURNAL:J. Am. Chem. Soc.
VOL:111 PAGE : 1452 -1455 (1989)
[TOP]

[1077]
AUTHOR:Porter,N.A., Logan,J. and Kontoyiannidou,V.
TITLE:Preparation and Purification of Arachidonic Acid Hydroperoxides of Biological Importance.
JOURNAL:J. Org. Chem.
VOL:44 PAGE : 3177 -3181 (1979)
[TOP]

[1078]
AUTHOR:Boeynaems, J. M., Brash, A. R., Oates, J. A., and Hubbard, W. C.
TITLE:Preparation and assay of monohydroxy-eicosatetraenoic acids PubMed ID:7004263
JOURNAL:Anal Biochem.
VOL:104 PAGE : 259-267 (1980)
[TOP]

Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.